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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 taking in a stunning sunset over Lake Michigan, we’ve got you covered. Let’s explore the top things to do in Chicago!
Don’t Miss Out On Our Top Choice
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did in Chicago is this architecture river cruise. It covers all three branches of the river and hits iconic sights like the Wrigley Building and John Hancock. The live guide shares fun local stories—and there are tours running all day!
- Don’t Miss Out On Our Top Choice
- Things to do in Chicago, Illinois
- 1. Experience Chicago’s best sights and foods on a walking and tasting tour
- 2. See the city from a Chicago River Cruise
- 3. Discover Chicago’s infamous crime and mob history
- 4. Visit the Art Institute of Chicago with skip-the-line entry
- 5. Take a relaxing sunset cruise on Lake Michigan
- 6. See Chicago’s impressive architecture on a walking tour
- 7. Find hidden gems and taste the city’s best donuts with a local guide
- 8. Explore Chicago on a Segway
- 9. Take a bicycle, bites, and brews tour of the city
- 10. Visit the Medieval Torture Museum
- Where to Stay in Chicago
- Thanks for reading!
- Why We Book Tours with Viator
- Renting a Car in the USA
- Don't Forget Travel Insurance!
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: 4.8 stars (check 1,400+ 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
- 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 14,000+ 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!
Book this top-rated river cruise here and enjoy free cancellation!
3. 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 2,700+ 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!
4. 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 200+ 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!
5. Take a relaxing sunset cruise on Lake Michigan
- Duration: 1.5 hours
- 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 1,200+ 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.
But for that reason, it always sells out well in advance, so don’t hesitate to book your spot now!
Book this sunset cruise here while spaces are still available!
6. See Chicago’s impressive architecture on a walking tour
- Duration: 2 hours
- Time: 11 am and 1 pm
- Highlights: Exploring Chicago’s Loop area, admiring the neighborhood’s architectural marvels, discovering hidden gems on a carefully curated route
- Inclusions: Local guide, small group tour
- Rating: 5 stars (check 1,000+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Chicago is home to some of the U.S.’s most impressive architecture, so exploring it on this walking tour is a must. It gave me the chance to explore Chicago away from the typical tourist spots and I even got to go into some of the city’s most fascinating interiors.
Our guide, Kaylee, was knowledgeable and lively with an infectious passion for architecture. She shared lots of interesting facts about the city’s rich history and architectural evolution as we followed her carefully curated route around the hidden nooks of Chicago’s Loop.
We started at the iconic Chicago Board of Trade Building, an Art Deco marvel that took my breath away with its intricate details and grand design. From there, we ventured into other buildings to admire some of the most ornate lobbies and staircases I have ever seen.
I especially loved seeing the stained glass mosaics. One of the best parts was the Chicago Cultural Center, which boasts an absolutely breathtaking interior.
This tour made me feel like I had uncovered a new side of Chicago that I would never have found on my own. Even though I’m not a huge architecture buff, I was fascinated by this tour and I’m so glad that I decided to do it. And so are at least a thousand other people, according to all of the 5-star reviews!
Don’t hesitate—book your spot on this top-rated architecture tour here!
7. 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 1,200+ 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 dreamy donut tour here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
8. Explore Chicago on a Segway
- Duration: 2 hours
- Time: Multiple times slots available between 10 am and 4 pm (not available Tuesday)
- Highlights: Fun Segway ride exploring Millennium Park, the Buckingham Fountain, the Museum Campus, or Riverwalk tour discovering the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue, and passing by Millennium Park
- Inclusions: Use of Segway, helmet, local guide, small-group tour
- Rating: 4.8 stars (check 400+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
This Segway tour of Chicago is SUCH a fun way to explore the city. It made me feel like I was a kid again as I zoomed along the city streets, and I had a huge smile on my face the entire time!
To be honest, I was nervous about balancing on the Segway at first, but our guide was really patient and made sure everyone felt comfortable before we took off. Within minutes, I was gliding effortlessly through the streets, feeling like a total pro.
We rolled through Grant Park with skyline views, stopped at Buckingham Fountain, and cruised along the lakefront by the Museum Campus. The Segway made it easy to cover a ton of ground without getting tired, and the commentary brought Chicago’s history to life—from the Great Fire to the stories behind the architecture.
This tour is great for families with older kids (minimum age is 10) or anyone who wants to try something a bit different.
Not into Segways? No worries—there’s something for everyone. A Riverwalk tour lets you explore the Chicago River area on foot, with stops at Navy Pier, iconic bridges, and a stroll along historic Michigan Avenue past Millennium Park. It’s a more relaxed pace but still packed with city highlights.
No matter which option you choose, you’ll experience some of the best views and stories Chicago has to offer—just the way you like it!
Check availability and book this tour here!
9. Take a bicycle, bites, and brews tour of the city
- Duration: 4.5 hours
- Time: 11:30 am or 5:30 pm
- Highlights: Exploring Chicago on a bicycle, trying local foods like hot dogs and deep dish pizza, sampling local brews, choice of two exciting routes
- Inclusions: Use of bicycle, helmet, food and beverage tastings, expert local guide, water bottle
- Rating: 4.9 stars (check 600+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Biking through Chicago while indulging in its most iconic foods? Sign me up! This small-group bicycle tour was the perfect mix of sightseeing, exercise, and, most importantly, delicious eats and amazing local drinks.
We started at the bike shop, where our guide gave us a quick rundown on safety before we hit the road. The route took us through some of the city’s most vibrant neighborhoods, and I loved how we got to see both the classic landmarks and some lesser-known spots.
We rode past the historic Wrigley Field, cruised through the charming streets of Old Town, and soaked in the lakefront views from Lincoln Park!
Of course, the real star of the tour was the food. Our first stop was for a classic Chicago dog, which was piled high with mustard, relish, onions, tomatoes, a pickle spear, sport peppers, and a dash of celery salt. No ketchup, of course!
Next, we sampled deep-dish pizza which was everything I hoped for. Then, we finished off with a rich, fudgy brownie. Did you know that brownies were actually first created right here in Chicago?
Cycling can be thirsty work, but thankfully, we got to try some refreshing local brews en route, too! We got the true Chicago experience on this tour. It was the perfect blend of adventure and indulgence—no wonder it has over 600 5-star reviews!
Book this cycling tour here and enjoy FREE cancellation up to 24 hours in advance!
10. Visit the Medieval Torture Museum
- Duration: 1.5 hours
- Time: Entry between 10 am and 9 pm
- Highlights: Huge interactive torture museum, seeing gruesome medieval torture devices, realistic wax sculptures, audio guide for deeper insights, bonus ghost-hunting app experience
- Inclusions: Museum entry, audio guide, ghost hunting app, all taxes and fees
- Rating: 4.8 stars (check 700+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
I’m so glad we booked tickets to the Medieval Torture Museum while we were in Chicago. We were absolutely fascinated to discover this dark chapter of U.S. history. It’s not exactly a lighthearted experience, but it is incredibly engaging and a must for fans of true crime or horror movies.
This museum is super well thought out. The dim lighting, eerie music, and lifelike wax figures set an unsettling tone from the moment we arrived.
The artifacts took us through gruesome methods of torture, punishment, and execution from centuries past. All of the exhibits were incredibly detailed and covered everything from the infamous Iron Maiden to spine-chilling interrogation devices we had never even heard of before.
Each display came with well-researched descriptions, and the audio guide provided us with even more horrifying context. We found ourselves both fascinated and disturbed by how creative (and cruel) humans have been when it comes to punishment.
The ghost-hunting app added an extra thrill to the visit. At first, I’ll admit we both thought that it was just a fun gimmick, but as we wandered the museum, we couldn’t shake the feeling of being watched. Whether or not you believe in the paranormal, it definitely enhanced the eerie atmosphere!
We ended up spending over two hours exploring, and next time we’re in Chicago, we’ll probably go back for more. This museum isn’t for the faint of heart, but if you love history, horror, or anything macabre, it’s an unmissable Chicago attraction.
Grab your tickets to the Torture Museum here!
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!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
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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