15 Best Things to do in Chicago, Illinois 

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Planning a trip to Chicago? You’re in the right place!

We love exploring the Windy City. From its iconic skyline and deep-dish pizza to its world-class museums and lively neighborhoods, Chicago is packed with incredible experiences. But with so much to see and do, figuring out where to start can feel overwhelming!

That’s why we’ve put together this guide to help you make the most of your time in Chicago. Whether you’re cruising down the river on an architecture tour, diving into the city’s mob history, tasting legendary local eats, or exploring iconic museums, we’ve got you covered. Let’s explore the top things to do in Chicago!

Things to do in Chicago, Illinois

1. Experience Chicago’s best sights and foods on a walking and tasting tour

• Duration: 3 hours 
• Time: 11 am, 11:30 am, or 5:30 pm 
• Highlights: Visiting iconic highlights like Millennium Park and the Palmer House Hotel, tasting quintessential Chicago foods like deep-dish pizza and hot dogs, visiting local favorite eateries
• Inclusions: Local guide, all food tastings amount to a full meal, bonus 2-hour kayak or bike rental
• Rating: 4.9 stars (check 1,900+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Chicago is a city that knows how to eat, and this food tour is proof of that! We loved visiting local hotspots and indulging in the city’s most indulgent dishes. 

Honestly, the pizza alone is worth booking this tour for! I know that Chicago pizza divides opinions, but I loved it. For me, the thick, buttery crust and layers of gooey cheese really hit the spot. You’ve got to try it while you’re here and see what you think!

I also enjoyed strolling down the city’s Magnificent Mile, where we visited a classic hot dog stand and got to taste a true Chicago-style dog, which means a beef frankfurter, lots of pickled toppings, and no ketchup! 

Just when I thought I couldn’t eat any more, we arrived at the Palmer House Hilton to try the famous brownies. The recipe hasn’t changed for over a century, and with good reason. You can’t improve on perfection, after all!

Beyond the food, this tour was also a fantastic way to see the sights of Chicago. We walked through Millennium Park, saw the iconic Bean, and strolled along the river. Oh, and we got to choose between a FREE two-hour kayak or bike rental afterwards, so it was great value for money, too.

And I have to give a shoutout to our guide, Jeff, who was an absolute delight. He was so charismatic and friendly, so I wasn’t surprised to see his name mentioned time and time again in all of the glowing reviews!

Don’t miss out—book your spot on this top-rated food tour here!

2. See the city from a Chicago River Cruise

• Duration: 1 hour (Note: only available from mid-March to November)
• Time: Multiple time slots between 9 am and 9:20 pm 
• Highlights: Relaxing river cruise, passing by famous landmarks like the Wrigley Building and the John Hancock Building, covering multiple branches of the Chicago River, learning insider facts and stories, expert commentary on the city’s architecture
• Inclusions: One-hour river cruise, live commentary, restroom on board 
• Rating: 4.8 stars (check 15,700+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

If you do only one thing in Chicago, make it this river cruise! Hands down, this was my favorite experience in the city. There’s just no better way to take in the stunning skyline than from the water, with the buildings rising up around you like an open-air architecture museum!

Our onboard guide, Kevin, had an infectious passion for Chicago’s history. As we floated down the river, he told us stories about the Great Chicago Fire, the birth of the skyscraper, and how the city literally reversed the direction of the river. I never knew that engineering could be this fascinating!

Meanwhile, we saw so many fantastic sights, from iconic structures like the sleek Aqua Tower, the gothic Tribune Tower, and the legendary Wrigley Building. I had already walked these streets before this experience, but seeing them from the water was so much more impressive. 

This tour is a really fun and memorable experience but it’s also a really efficient way to see Chicago. Honestly, it’s a real must-do regardless of whether you’re a first-time visitor or have been here multiple times before. And you don’t just have to take my word for it because there are over TEN THOUSAND 5-star reviews!

Please note that this is only available from mid-March to November, as it gets too cold for this to be an enjoyable winter experience!

Book this top-rated river cruise here and enjoy free cancellation!

3. Check out the Willis Tower SkyDeck

• Duration: 30 minutes–1.5 hours
• Time: Multiple times available from 9 am–9 pm 
• Highlights: Ride to the 103rd floor of Willis Tower with skip-the-line entry, explore the interactive Chicago Experience, step onto the glass Ledge for unbeatable views of Chicago’s skyline and lakefront
• Inclusions: Skydeck admission, access to The Ledge, a glass-floored balcony perched 4.3 feet (1.3 meters) outside of Willis Tower, video and interactive exhibits
• Rating: 4.3 stars (check 1,700+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

For a classic Chicago moment that never gets old, this takes you straight to the Skydeck at Willis Tower—and yes, the views really are as wild as everyone says. With these prebooked tickets, you skip the long ticket lines entirely and head straight inside at your chosen time, which is a huge win on busy days.

Once you’re in, you’ll pass through the Chicago Experience, a massive 45,000-square-foot (4,180-square-meter) exhibit filled with interactive displays, fun photo moments, and little bits of history that give you a real sense of the city’s character. It’s a great warm-up before you jump into the high-altitude excitement.

From there, the elevator rockets you up 103 floors in seconds. When the doors open, you’re met with uninterrupted views of the skyline, the lake, and big-name spots like Navy Pier, Wrigley Field, and Millennium Park‚—all from 1,353 feet (412 meters) in the air. On clear days, you can see up to 50 miles (80 kilometers) out.

And if you’re feeling bold, step onto The Ledge: a glass balcony that extends 4.3 feet (1.3 meters) outside the building. It’s the kind of heart-pounding moment that turns into a favorite Chicago memory.

You can stay as long as you like at the top, taking photos or just soaking it all in. Just make sure to book this tour early so you can lock in the exact time you want, especially if you’re aiming for those golden sunset views.

Reserve this popular activity here and get FREE 24-hour cancellation!

4. Discover Chicago’s infamous crime and mob history

• Duration: 1.5–2 hours 
• Time: Multiple time slots between 10 am and 8 pm 
• Highlights: Seeing where famous criminals like Al Capone and John Dillinger hung out and Prohibition-era tunnels, visiting storied locations from Chicago’s criminal past, such as Holy Name Cathedral, learning about the St. Valentine’s Day Massacre
• Inclusions: Transport in a luxury air-conditioned bus, historian guide, exclusive crime quiz, keepsake brochure with special offers, mini mob museum
• Rating: 4.6 stars (check 3,100+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

If you love true crime, history, or just a good story, this Chicago gangster tour is an absolute must! It’s one thing to hear about Al Capone, John Dillinger, and the St. Valentine’s Day Massacre, but it’s quite another to stand where it all happened! 

For two hours, we were chauffeured around the city in a comfy, air-conditioned coach, but in reality, it felt like we were being transported back in time to Prohibition-era Chicago. Our guide, Jay, was a talented storyteller but also had us laughing a lot as she weaved tales about the Windy City’s infamous mobsters. We even saw the courthouse where many of them were prosecuted!

One of the most chilling stops was the Biograph Theatre, where the notorious gangster John Dillinger was gunned down by the FBI. I actually got goosebumps while hearing the story of his final moments.

We also visited Holy Name Cathedral and learned about the brutal assassination of Hymie Weiss right outside its doors. But I think visiting the site of the St. Valentine’s Day Massacre in Lincoln Park was the most eerie of all, especially once we were filled in on the violent events that unfolded there.

The tour had the perfect mix of bus time and opportunities to hop off, stretch our legs, and take pictures. It’s definitely not your run-of-the-mill sightseeing tour, and it’s a super unique and engaging way to get to know Chicago’s history. True crime fans can’t miss this one!

Check availability and book this tour here!

5. Visit the Art Institute of Chicago with skip-the-line entry 

• Duration: 2.5 hours 
• Time: 10:30 am, 2 pm, or 5 pm (not available Tuesday)
• Highlights: Skip-the-line entry, learning the background behind famous paintings, private or semi-private tour tailored to your interests, seeing artwork by artists like Picasso and Warhol 
• Inclusions: Professional guide, skip-the-line museum entry, private or semi-private guide (depending on option selected)
• Rating: 5 stars (check 250+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

The Art Institute of Chicago is one of the most celebrated art museums in the world, so booking this guided tour is a must for any art lover! You can opt for a semi-private or private guided tour, depending on what fits your style. And with so much to see, having an expert lead the way is the perfect way to take it all in without feeling overwhelmed.

What we love the most about this tour is that it includes skip-the-line entry to the museum. We would have been waiting for well over an hour otherwise! Plus, our guide, Heath, made the experience ten times more interesting. He weaved fascinating stories into every masterpiece we saw. 

Some of the highlights in the museum include Seurat’s Sunday on La Grande Jatte, Hopper’s Nighthawks, and Picasso’s The Old Guitarist. Seeing these paintings in person makes them so much more powerful.

One of my favorite stops was definitely Marc Chagall’s America Windows, which is a vibrant blue stained-glass piece. I also loved getting a glimpse into the surreal world of Salvador Dali with Inventions of Monsters.

Whether you’re an art novice or a seasoned museum-goer, this tour is the best way to experience the Art Institute. It turned what could have been an overwhelming visit into an unforgettable journey through some of the world’s greatest masterpieces. And don’t just take our word for it because you can read hundreds of 5-star reviews here.

Book this guided Art Institute tour here and enjoy FREE cancellation!

6. Walk the Magnificent Mile

A walk along the Magnificent Mile is one of those quintessential Chicago experiences that feels exciting no matter how many times you’ve done it. This 13-block stretch of Michigan Avenue is packed with luxury shops, historic landmarks, and some of the city’s most impressive architecture—making it a perfect place to wander, browse, and soak up the energy of downtown.

As you stroll, you’ll pass famous buildings like the Wrigley Building and the Tribune Tower, both unmistakable with their striking facades and riverfront locations. Even if you’re not in the mood for serious shopping, it’s fun to pop into spots like Tiffany & Co. or Saks Fifth Avenue just to experience the elegance and window-shop your way down the street.

The Mag Mile isn’t only about retail, though. It’s also home to cultural gems like the Museum of Contemporary Art and the Chicago Architecture Center, which offer an easy way to turn a simple walk into a deeper dive into the city’s creative side. And with endless cafés, restaurants, and bakeries tucked along the route, it’s easy to break up your walk with a coffee, a quick bite, or even a full meal.

Whether you go for the shopping, the architecture, or the atmosphere, the Magnificent Mile is a must-do that showcases Chicago at its most lively and polished.

7. Take a relaxing sunset cruise on Lake Michigan

• Duration: 1.5 hours (Note: only available from mid-March to November)
• Time: Varies between 5:15 pm and 7:30 pm 
• Highlights: Relaxing boat cruise, admiring the skyline, seeing the city light up in the evening, cruising out into Lake Michigan to watch the sunset, unique perspective of Chicago
• Inclusions: 1.5-hour boat ride, climate-controlled lounge, restroom on board, expert local guide
• Rating: 4.5 stars (check 1,500+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

This sunset cruise is the BEST way to spend an evening in Chicago! There’s truly nothing like watching the city transition between a golden-hour glow to a sparkling nighttime skyline while gliding along the water.

Our experience began on the Chicago River, winding past some of the city’s most famous buildings, such as the Hancock Center and the Aqua Tower. Our guide was full of interesting facts, pointing out details we wouldn’t have noticed on our own. But the real magic happened when we passed through the locks and entered Lake Michigan! 

From out on the lake, the city looked just like a postcard with its reflection shimmering on the water. We grabbed drinks, found a perfect spot on the open deck, and watched as the sky turned pink and orange before fading into deep blue.

Just when I thought it couldn’t get any better, the skyline began to light up which was absolutely breathtaking. I think that this is the most magical thing you can do in Chicago, and it would be perfect for a romantic evening!

A cruise is the perfect way to take in Chicago from a fresh perspective without the crowds or the rush of street-level sightseeing. It’s also such a great way to get out on the water of the famous Lake Michigan and experience the kind of serenity that you just can’t find downtown.

Please note that this is only available from mid-March to November, as it gets too cold for this to be an enjoyable winter experience!

Book this sunset cruise here while spaces are still available!

8. Discover Chicago’s prohibition history & architecture

• Duration: 2.5 hours
• Time: 10 am and 1 pm 
• Highlights: Walk Chicago’s riverfront and skyline landmarks, learn how Prohibition shaped the city, explore sights like The Bean and the Wrigley Building, enjoy surprise local treats
• Inclusions: See iconic landmarks and architectural gems, stroll the Chicago Riverwalk, enjoy Chicago-style popcorn, English-speaking guide, get insider tips, small-group or private tour
• Rating: 4.9 stars (check 100+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

If you love walking tours that mix history, architecture, and great local treats, this small-group tour is one of the most fun ways to see Chicago. It traces the city’s Prohibition-era past while guiding you along some of the most famous landmarks in the downtown core—all with a local guide who keeps the stories flowing.

You’ll start beneath the glowing marquee of the Chicago Theatre before weaving through the streets toward the Pedway, an underground tunnel system locals actually use to dodge weather. From there, the route opens up into plazas and river viewpoints, with stops at highlights like the Picasso sculpture, Daley Plaza, and Chicago’s unmistakable skyline reflected in the river.

As you walk, you’ll learn how the city’s bootlegging years shaped neighborhoods, architecture, and culture, something most visitors never hear about. You’ll also pass icons like the Wrigley Building, Tribune Tower, the Magnificent Mile, and architectural gems such as the Jewelers Building and London House.

Weather permitting, the tour continues along the Chicago Riverwalk, where you’ll get postcard-worthy views and enjoy classic Chicago-style popcorn for a fun little treat included along the way. 

The tour wraps up at Millennium Park at the Bean, and if you prefer an even more personalized experience, there’s also a private option. It’s a great choice for families, couples, or anyone who wants more flexibility and dedicated time with the guide.

Book this small-group tour here and see the city’s history up close!

9. Have deep-dish pizza

Trying deep-dish pizza in Chicago isn’t just about grabbing a meal—it’s practically a rite of passage. And while locals may never agree on which place does it best, two names always rise to the top: Giordano’s and Lou Malnati’s. If you want the full experience, the fun thing to do is try both and decide where you stand in the great deep-dish debate.

Giordano’s is famous for its stuffed deep-dish style, which means you’re getting a seriously hearty pie with layers of cheese tucked between two crusts and topped with a thick spread of tomato sauce. It’s rich, indulgent, and so dense that even one slice feels like a full meal. People who love Giordano’s usually swear by the cheese pull—and they’re not wrong.

Lou Malnati’s, on the other hand, has a lighter, more buttery crust that still holds up to generous toppings without feeling overly heavy. Their signature is a savory sausage patty that covers the entire pizza, giving every bite that classic Chicago flavor. For many locals, Lou’s strikes the perfect balance between crispy, cheesy, and saucy.

The best part? Both spots have locations all over the city, so it’s easy to fit a deep-dish taste test into your Chicago itinerary. No matter which team you end up on, you won’t leave hungry!

10. Find hidden gems and taste the city’s best donuts with a local guide

• Duration: 2 hours 
• Time: 9 am, 10 am, or 12 pm 
• Highlights: Visiting the best donut spots around, discovering locally loved locations that tourists miss, trying lots of different donuts, exploring the downtown Loop neighborhood
• Inclusions: Guide, food tasting, vegan, gluten-free, and nut-free options available 
• Rating: 4.9 stars (check 1,300+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

A donut tour in Chicago? Sign us up! As self-proclaimed donut enthusiasts, this donut tour was pretty much a dream come true. Not only did we get to indulge in some of the city’s best sweet treats, but we also got a fun and engaging walking tour of downtown Chicago’s Loop.

Our guide, Nick, was fantastic. He was a super down-to-earth guy and a born-and-bred Chicagoan, so he was the perfect person to lead this kind of adventure! 

First up, he took us to the iconic Doughnut Vault, a cozy spot where we tried some very decadent glazed donuts. From there, we continued onto three other beloved spots where we tried donuts of every style and flavor, from crunchy old-fashioned buttermilk donuts to red velvet bites. I honestly didn’t know that so many different kinds of donuts even existed before doing this tour!

The walking aspect of the tour was a great way to balance out the indulgence (or at least that’s what we told ourselves), and the city’s vibrant energy made it all the more enjoyable.

By the end, we were happily stuffed and definitely had a newfound appreciation for Chicago’s donut scene. If you love donuts—and who doesn’t—this tour is an absolute MUST! 

Book this tasty donut tour here!

11. See Chicago from a helicopter

• Duration: 45 minutes
• Time: Multiple times available from 9 am–8 pm 
• Highlights: Enjoy a private helicopter flight over Chicago, soar past skyline icons, with unbeatable aerial photo opportunities and clear narration via noise-canceling headsets
• Inclusions: All Fees and Taxes, live commentary on board, noise-cancelling headsets, parking, photos of and in front of the helicopter, private tour
• Rating: 4.8 stars (check 120+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

For a truly unforgettable way to experience Chicago, this private helicopter tour lets you see the city from a whole new perspective. It’s a 45-minute flight designed for up to three people, making it an incredible option for special occasions, celebrations, or simply upgrading your trip with something you’ll be talking about long after you land.

Once you’re buckled in with noise-cancelling headsets, your pilot will guide you up and over Chicago’s most famous landmarks. You’ll soar past Millennium Park, Navy Pier, the John Hancock Center, Soldier Field, and even Wrigley Field—all without the crowds or the traffic below. The panoramic views of the skyline and Lake Michigan are nothing short of stunning, especially when the light hits the skyscrapers just right.

Along the way, your pilot provides live commentary, pointing out local landmarks, fun facts, and hidden details you’d never notice from the ground. You’ll also pass over icons like the United Center and the Museum Campus, with plenty of chances for jaw-dropping photos from the air.

Since it’s a private tour, you get the entire helicopter to yourselves, which means more comfort, more flexibility, and a far more personalized experience. Plus, free parking and complimentary photos (your pilot doubles as an excellent photographer!) make the whole outing even more fun.

Book this private helicopter tour here and see Chicago from above!

12. Explore Wicker Park

Wicker Park is often called Chicago’s coolest neighborhood, and it’s easy to see why. This artsy, bohemian area is full of colorful street art, independent shops, local galleries, craft coffee, and live performance spaces. It’s the kind of place where you can wander without a plan and stumble into something interesting on every block. 

Here are some of the best things to check out in the neighborhood:

• Myopic Books – This iconic used bookstore feels like a maze, with shelves stacked to the ceiling and cozy corners perfect for browsing. You can easily lose track of time searching for hidden gems.

• Flatiron Arts Building – A creative hub filled with galleries, studios, and rotating exhibits. There’s always something happening here, from art openings to small performances. It’s a great place to experience Wicker Park’s artistic side.

• Milwaukee Avenue – The main strip of the neighborhood and the heart of its energy. Expect vintage shops, record stores, boutiques, cafés, and some of the best people-watching in Chicago.

• Murals & street art – Wicker Park is known for its bold, colorful murals scattered throughout the neighborhood. The Vivian Maier mural is a favorite, and while the Greetings from Chicago mural sits just outside Wicker Park, it’s an easy detour and well worth the stop.

• The Den Theatre & local venues – If you love live entertainment, The Den Theatre is a favorite for comedy, plays, and intimate performances. Wicker Park also has several small music venues where you can catch local bands and up-and-coming artists.

13. Customize your city experience with a private guided tour

• Duration: 3–4 hours 
• Time: 10 am and 2:40 pm 
• Highlights: See Chicago’s top landmarks in just a few hours, including Millennium Park, Lincoln Park, Museum Campus, and Wrigley Field, with a comfortable drive through the city’s most iconic neighborhoods
• Inclusions: Driver/guide, local guide, transportation, hotel pickup, private customized tour 
• Rating: 4.9 stars (check 200+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

When you’re short on time but want to see as much of Chicago as possible, this private driving tour is one of the easiest and most efficient ways to explore the city. Because it’s completely private and customizable, you can work with your guide to focus on the places you’re most excited about.

Your guide picks you up directly from your downtown hotel, so there’s no extra planning or navigating required. From there, you could head to Millennium Park for a guided stroll by the iconic Bean before making your way through the Loop’s historic architecture and buzzing street life. It’s an excellent introduction to downtown Chicago.

The tour can also take you north to Lincoln Park and its surrounding neighborhoods, where you’ll get a feel for local Chicago living while enjoying plenty of greenery and lakeside views. On the city’s South Side, you can explore the beautiful campus of the University of Chicago in Hyde Park—a spot many visitors never think to see.

Sports fans often request a stop at Wrigley Field to admire the historic stadium, but your guide can tailor the itinerary to your interests, whether that means more architecture, more parks, more neighborhoods, or a mix of everything.

No matter how you design it, this tour gives you a relaxed, personalized way to see the city without worrying about logistics or time limits!

Book this customizable tour here to see Chicago exactly how you want to!

14. Stop by the Field Museum

The Field Museum is one of Chicago’s most impressive attractions and one of the largest natural history museums in the world. Whether you’re visiting with family, exploring on your own, or trying to fill a rainy-day gap in your itinerary, this is the kind of place that pulls you in and keeps you wandering for hours.

You’ll find everything from ancient Egyptian artifacts to sparkling gemstones, prehistoric fossils, and cultural exhibits from around the globe. One of the museum’s most famous residents is “SUE,” the largest and most complete T. rex skeleton ever discovered. It’s a must-see for anyone even remotely interested in dinosaurs. Nearby, the Evolving Planet exhibit walks you through billions of years of natural history, and the Grainger Hall of Gems is a favorite for its dazzling displays.

The Field Museum is huge—spread across multiple floors with enough variety to appeal to every type of traveler. Most people spend three to four hours exploring, but if you’re a museum lover, you could easily spend most of the day here. Tickets start at $30 USD, and visiting early in the day can help you avoid larger crowds.

With its world-class exhibits and endless things to explore, the Field Museum is a Chicago essential for anyone interested in history, science, or simply seeing something truly remarkable.

15. Explore Navy Pier

Navy Pier is one of Chicago’s most iconic waterfront spots, stretching out into Lake Michigan and offering something fun in every season. With attractions, restaurants, shopping, and frequent events, it’s an easy place to spend a few hours and enjoy classic Chicago lakefront views.

One of the highlights is the Centennial Wheel, which lifts you 200 feet (61 meters) above the lake for panoramic skyline views. In the warmer months, Navy Pier comes alive with outdoor beer gardens, live music, public art displays, and bi-weekly summer fireworks that light up the sky. If the weather isn’t ideal, you can head indoors to explore places like the Chicago Children’s Museum or catch a show at one of the pier’s theaters.

The pier also has plenty of places to grab a meal or snack, from casual bites to sit-down spots with views of the water. And with hotels located right on the pier, some visitors even choose to stay here for the unbeatable proximity to both Lake Michigan and downtown.

Before visiting, it’s worth checking the pier’s event calendar here—Navy Pier often hosts festivals, performances, and rotating seasonal activities that add even more to the experience.

Whether you’re riding the wheel, enjoying the lake breeze, or simply exploring, Navy Pier is a must-see Chicago landmark.

Related Read: Need help planning your trip? Follow our 3-day Chicago itinerary to see these top sights, and more!

Where to Stay in Chicago

Chicago is the third-largest city in the United States, so deciding where to stay can be tricky! Our advice would be to stay in the Loop! It’s a fun downtown area that encompasses many of the city’s top attractions, and lots of the activities we’ve mentioned in this blog start and end here.

We’ve made it easy for you by choosing three of our favorite hotels in the Loop. There’s something for every budget, and each property has excellent reviews. So keep on reading and decide which one suits you best!

Luxury – $$$ 

The Langham Chicago is a luxurious 5-star hotel just two blocks from the Magnificent Mile, so you really couldn’t choose a better location. It’s housed in a gorgeous skyscraper designed by Mies van der Rohe, a famous German-American architect. The rooms ooze elegance, and the bathrooms are the stuff that dreams are made of, with marble surfaces and deep soaking tubs.

Perhaps the only trouble with this hotel is that you’ll never want to leave the property! And with a state-of-the-art fitness center, a refined afternoon tea experience, and one of Chicago’s top-rated restaurants on offer, I really wouldn’t blame you.

Prices at the Langham start at $550 USD per night. Check out all of the options and book this luxurious stay on Booking.com now!

Mid-range – $$ 

Located in the heart of downtown Chicago, Club Quarters Hotel Central Loop offers a comfortable and convenient stay just a short walk from the Willis Tower Skydeck and Quincy/Wells Subway Station. It doesn’t get much more convenient than that! The modern rooms offer everything you need, including free WiFi, a flat-screen TV, and a coffee machine with complimentary bottled water. But perhaps the main reason that we love this place is because of its in-house English-style pub, which offers over 100 varieties of beer and scotch whiskey. 

Prices here range between $180 USD and $400 USD per night. Check availability for your travel dates and reserve your stay on Booking.com!

Budget – $ 

Budget stays in Chicago don’t get much better than the HI Chicago Hostel. This is a clean and modern spot that’s located in the vibrant South Loop, so it’s perfect for exploring the city’s buzzing nightlife, top museums, and world-class dining. There are 4- to 10-bed dorms available as well as private rooms, and breakfast is included! With a welcoming atmosphere, shared spaces to meet fellow travelers, and an unbeatable location, this hostel is the ideal base for soaking up Chicago’s energy without breaking the bank.

Dorm beds here typically start at about $35 USD and private rooms at about $110 USD per night, with private options starting at $115 USD. Check out all of the options and book your stay over at Booking.com!

For more options, see all of Chicago’s listed hotels here!

Renting a Car in the USA

The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.

We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.

Tips for Renting a Car in the USA

• Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
• Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
• Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
• Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.

What You Need to Rent a Car in the USA

• A valid driver’s license from your home country.
• An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
• A credit card in the driver’s name is typically required for the security deposit.
• Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.

Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!

Thanks for reading!

Chicago really is one of those cities that leaves a lasting impression. Between the skyline views, legendary eats, deep-rooted history, and lively neighborhoods, there’s no shortage of things to do—and we hope this guide made planning your trip a little easier. Whether you’re diving into crime stories, cruising down the river, or simply devouring deep-dish pizza, there’s something here for everyone.

Want more travel ideas? Head over to our USA blog section where we share even more city guides, travel tips, and personal favorites! Or check out a few popular guides below for nearby destinations.

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