Chicago
Meet the Locals

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Our most recommended Chicago Meet the Locals

Chicago Underground Donut Tour

1. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

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Chicago: Food, Architecture and History Tour

2. Chicago: Food, Architecture and History Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago). Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination where you can sample locally made chocolate from a Chicago staple. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. End up in the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience.  Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Start your food tour with a well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has their own preference as to how the dog should be made, and you’ll get a chance to try your guides’ favorite version. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef.  Sample this sandwich in a real Chicago institution. Your tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see and do in the city.

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Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

3. Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

Explore the complex layers of Chinese culture and the many contributions these people have made to both Chicago and the world. And what better way to show off Chinese culture then through food? Your guide will take the confusion and language barrier away as you sample your way through a variety of Chinatown's best restaurants and well-kept secret recipes. Start your tour at Phoenix Restaurant and begin with some yummy dim sum dumplings and a traditional Chinese tea tasting. Next, it will be time for a sweet treat - buttery custard tarts from Chinatown's oldest bakery. Then, try a unique and delicious spicy meat sandwich from the Xi'an region. Afterward, stroll through the charming Chinatown Square with its ethnic grocery stores and souvenir shops. Finally, taste a sampling of succulent dry chili chicken, followed by the famous spicy Szechuan hot pot. You'll have traveled all over China but only walked a few blocks on this delicious tour of one of Chicago's most fascinating neighborhoods.

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Chicago: West Loop Underground Donut Tour

4. Chicago: West Loop Underground Donut Tour

Experience the food scene in Chicago on this underground donut tour in West Loop. Learn how each donut location you visit fits into the larger food scene and history of Chicago. Feed your sweet tooth and try donuts from local shops while exploring Restaurant Row. Start at Chicago's French Market that's styled after European markets like those in Barcelona or Paris. Discover all kinds of delicious food and drinks along with the highlight of the trip: donuts. Then, walk along Restaurant Row in Chicago's West Loop. Learn the history of the area on your way to the next stop, Sawada Coffee, a hidden gem of the neighborhood. Next, visit one of the most popular donut shops in the West Loop, Do-Rite Donuts. Try one of their signature donuts, voted the best donut in the city for several years. End at BomboBar and enjoy a big finish to this sweet tour.

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Chicago: History, Culture and Architecture Walking Tour

5. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

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Chicago: River North Walking Food Tour

6. Chicago: River North Walking Food Tour

Come enjoy the luxury and opulence of the Magnificent Mile and Gold Coast on this guided food tour, a tour through the historically affluent River North neighborhood. Explore the remarkable and historic River North neighborhood known for its extreme affluence, typified by the Magnificent Mile and the Gold Coast. Boasting Chicago's highest concentration of restaurants and art galleries, the River North neighborhood has become a favorite destination for foodies. You will taste foods from five unique restaurants and bakeries, and your food tour guides are experts not only at temporarily filling stomachs, but at plumping up tour-goers' local food knowledge too. This 3-hour walking tour offers a look into the history and culture of the neighborhood in between each of your 5 food tastings. While the stops are subject to change, we usually stop to taste at five of the following food places: • The Doughnut Vault (est. 2011): Food and Wine Magazine named it the best doughnut in America in 2012 • Lou Malnati's (est. 1971): Rudy Malnati is generally considered to be the inventor of Chicago deep-dish pizza • Xoco- (est. 2009): Top Chef Masters winner Rick Bayless is one of the best known chefs for Mexican cuisine in America • Iberico- (est. 1992): Serving you the most authentic tapas and regional specialties from all across Spain • Al's Beef- (est. 1938): Founder Al Ferrari invented the sandwich in Chicago's Little Italy back in 1938 • Fabcakes Bakery- (est. 2012): Delicious pastries inspired by the seasons Your informative guide will point out examples of historic architecture and beautiful public spaces that help make the River North neighborhood one of Chicago's most notable.

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Chicago: Photo Shoot with a Private Vacation Photographer

7. Chicago: Photo Shoot with a Private Vacation Photographer

The tour provider will organize the locations for your photo shoot based on your own unique requirements, whether it be a family getaway, a romantic trip or a livelier one with friends.  Once the details are organized, you will receive confirmation of all the information you need, leaving you to simply meet the photographer on location in Chicago on the day and let them work their magic, capturing your travels in a contemporary and candid style of photography. Your Chicago vacation photographers are handpicked and highly experienced in addition to being local experts and will share their knowledge of the city with you like an old friend. Once your photo tour has finished, you will receive a link to your own personal online gallery (password protected) within 5 working days, containing your professionally edited images, all free to download. This photo tour will allow you to look back over your travels with fond memories, when all too often you are left with rusty memories of your journeys. Make sure that the next time you travel, you will have mementoes that will last a lifetime and beyond.

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Xplori 4G SIM Card for US

8. Xplori 4G SIM Card for US

Stay connected while traveling around the US with a 4G sim card from the leading mobile operator in the US, AT&T. Use your sim immediately — no need to register. Make calls to over 100 destinations worldwide for just $0.20/ minute.  Activation procedure: Please ensure that data and data roaming are turned on for your mobile device (for iOS: Settings > Mobile Data and Mobile Data Options; for Android: Settings > Mobile Networks). Wait for a few minutes for your mobile device and sim card to sync, restart your mobile device if this takes too long. If the sim cannot find the network by itself, please select ‘AT&T’ manually.

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Chicago: Riverwalk Guided Walking Tour

9. Chicago: Riverwalk Guided Walking Tour

Tag along on this essential Chicago experience: a guided walking tour of the Chicago Riverwalk. Spend your day exploring art, architecture, and all the locals’ favorite spaces. Visit the Meatpacking District, Chelsea Market, DuSable Bridge, and more. Birthed around the banks of the (now) Riverwalk, Chicago is a city teeming with tales. With the help of your local guide, discover the stories behind the sites you visit and see. Visit all four districts of the Riverwalk, each offering its own flavor of Chicago. Pass iconic sites including the Wrigley Building, Tribune Tower, DuSable Bridge, and the Marina Towers. As an added perk, become a Chicago insider with behind-the-scenes access at the McCormick Bridgehouse & Chicago River Museum. Stop at Heald Square and see the city’s many monuments and memorials. Along the tour, spot the touching Vietnam Veterans Memorial. Continue strolling down the Riverwalk and hear stories at the site of Old Fort Dearborn and the disaster that was the SS Eastland. Then, pass by the Jeweler's Building and find out if Al Capone really had a super-secret speakeasy at the very top. Nearing the end of the tour, take in a Picasso gifted to the city by the artist himself, see the first church at the Chicago Temple, and end under the prisms of light filtering in the Tiffany Dome at the Chicago Cultural Center.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.8 / 5

based on 153 reviews

The Chicago Underground Donut Tour was one of the highlights of the entire trip! I told my brother (a local) about it and two of the four stops were ones he loves to go to. Our tour guides, Addison and Jackson were awesome! They kept us laughing the whole time and were really personable and easy to talk to. I really enjoyed the variety of donuts I sampled at each shop. We actually went back to Firecakes a second time after this tour. Thanks for an unforgettable experience!

This was a lovely time! The hosts were amazing, the donuts were incredible, and it was overall just the best. What a way to start the day. The girlfriend and I took my new sailor daughter on the tour and it couldn't have been a better start to the day. The hosts were very knowledgeable of the area and were visibility excited to share anything and everything not only about the donuts but the city.

I had an amazing time on this tour! In my opinion, the walking tour allowed me to see so much more of the city, up close and from my own personal viewpoint. The tour guides were very friendly, funny, and knowledgeable. We were even given "Garrett's Popcorn" and "Fannie May Chocolate" as some sweet treats. I highly recommend this tour, and I'm so glad that I did it!!

Kelly, our guide, was phenomenal! We live in the Chicagoland suburbs so thought to take an official tour to learn more details than the obvious ones we already knew. Kelly fulfilled that with much knowledge, grace and charm. Had a wonderful tour and learned a lot!!!

Small group, only 10 on our tour. Our guide was Kevin and he did a great job. Very fun and informational. I highly recommend a smaller group.