Experience the best Chicago tours

Experience Chicago’s rich history, famous architecture, distinctive food culture, and more with our local guide by your side. From the Magnificent Mile to the Chicago River, you’ll see this city as you never have before.
Buckingham Fountain in Grant Park in Chicago
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The best way to see Chicago

Mobsters and deep dish pizza, skyscrapers and parks — there’s a lot Chicago is known for, but no one knows it as well as the locals who live here. Let us show you around. 

We recommend starting with the Riverwalk, discovering spectacular architecture and the river that fueled the city as it became a major Midwestern metropolis way back in the 19th century. Then take a deep dive into the heart of Chicago. We’re talking everything from local flavors to unsolved mob mysteries.

Curious to know more? Here’s a little about what makes our Chicago tours different.

  • We don’t just check off a bucket list. Sure, you’ll see The Bean, the former Sears Tower, and other icons, but we immerse you in the city with history, secrets and surprising stories.

Mobsters and deep dish pizza, skyscrapers and parks — there’s a lot Chicago is known for, but no one knows it as well as the locals who live here. Let us show you around. 

We recommend starting with the Riverwalk, discovering spectacular architecture and the river that fueled the city as it became a major Midwestern metropolis way back in the 19th century. Then take a deep dive into the heart of Chicago. We’re talking everything from local flavors to unsolved mob mysteries.

Curious to know more? Here’s a little about what makes our Chicago tours different.

  • We don’t just check off a bucket list. Sure, you’ll see The Bean, the former Sears Tower, and other icons, but we immerse you in the city with history, secrets, and surprising stories.
  • Our Chicago food tour (coming soon!) introduces you to the highlights of the city’s culinary scene so you can quite literally “taste Chicago” in just one afternoon.
  • Every tour guide is a local expert who can share insider tips on the top restaurants, museums, free attractions (we’ve got plenty), and more.

Our tours combine convenience and connection. Guides take care of the details so you can enjoy a stress-free visit, and they show you the best of their city in a way that goes beyond superficial sightseeing. We guarantee it will be an experience you’ll remember for years to come. We can’t wait to welcome you to Chicago!

What people are saying about our Chicago tours


Kevin really has great energy, you can tell he loves what he does. Fully recommend it.
— Maria

We had a really fun time on this tour! Leo was very informative and a great story teller. We learned more about the city and its history. I would strongly recommend this tour!
— Kate

10/10 would recommend! Loved the tour, learned a lot in a fun way. This was the first tour of this kind I did in my life and it was definitely one of my favorite experiences.
— Oriane

You can't miss this tour! We loved the tour, it was the best way to get to know and walk around the city. We had an amazing guide. We would definitely recommend this experience!
— Daryl

Really nice guide, many interesting facts about the Chicago architecture. The history of Chicago is amazing! Recommend this for everyone!
— Vlad

It was so informative!!!! Thank you very much Chris for the great tour! We loved your stories about the most important buildings next to the Chicago River
— Carola

Awesome! My wife & I enjoyed this tour. Ben was very informative and enthusiastic. He did a great job. I would recommend him to anyone.
— Chris

Our tour guide, Isabel, was a hoot and a half!!! So fun, so knowledgeable and so personable!!! Loved learning about the beautiful architecture!
— Tori

Entertaining and Knowledgeable! Kevin was knowledgeable and funny! Definitely recommend this tour for ghosts and gangster history enthusiasts!
— Katie

Love Chicago even more….. As someone who has lived in Chicago for many years it was fascinating hearing all the stories during the tour that I was unaware about.
— Dipak

Frequently asked questions about Chicago

What are the must-see landmarks in Chicago? 

As the nation’s third-largest city, Chicago is a must for anyone who likes good food, architecture, museums, parks and unique neighborhoods. There are quite a few spots that should definitely make it onto your wish list. Chicago’s lakefront is truly one of a kind, with The Art Institute of Chicago’s world-class art collection and one of the nation’s few free zoos, Lincoln Park Zoo, along with Millennium Park’s art sculptures and all-ages playground.

Slip into comfy walking shoes and stroll up the Mag Mile downtown, which curves over the Chicago River and features the city’s most revered shopping at designer boutiques. Then, walk along the Chicago Riverwalk for the best view of the city’s architecture.

Grab Chinese fusion at Top Chef winner Stephanie Izard’s Duck Duck Goat in the trendy Fulton Street Market or celeb chef Rick Bayless’ Mexican fare at Frontera Grill or Topolobampo in River North, followed by Instagrammable drinks at The Aviary. Get a glimpse of the city’s glittering skyline after dark at Skydeck Chicago, inside Willis Tower, the third-tallest skyscraper in the Western Hemisphere.

What are the best attractions in Chicago for families?

Chicago visitors with little ones should take full advantage of Lincoln Park Zoo, perched near the lakefront in the North Side neighborhood of Lincoln Park. If downtown, and need to stretch your legs, Millennium Park along North Michigan Avenue features art installations, green space and a playground.

 Here are a few more Chicago attractions great for families:

  • Within the Griffin Museum of Science and Industry’s permanent collection are a full-size replica coal mine, Apollo 8’s command module and a replica early-20th Century Chicago “Main Street.”
  • Explore nature and science exhibits at the Peggy Notebaert Nature Center.
  • Walk out onto Navy Pier, a collection of indoor shops and restaurants.
  • Older kids with an eye for art might like wandering through galleries at the Art Institute of Chicago, the country’s second-largest art museum after the Metropolitan Museum of Art in New York City, and home to the most haystack paintings by French impressionist Claude Monet.
  • Learn about astronomy at the Adler Planetarium, the country’s first planetarium and in Chicago since 1930.

What are the best tours in Chicago?

There’s so much to see and do in Chicago, especially given that this city has a lot of history. Dig into the dark side of the country’s third-largest city on the Mobsters and Haunted Mysteries of Chicago Walking Tour.

Looking for an opportunity to fill your camera roll with beautiful pics? Chicago is famous for its architecture, and you can see and learn about some of the best on the Chicago Riverwalk Architecture Tour.

When is the best time to visit Chicago?

Everything you’ve heard about Chicago winters is true: It’s windy, cold and dark. The best times of year to visit are late spring and early fall, the shoulder seasons surrounding summer. 

Attractions can feel crowded in the summer, particularly on weekends, so if you must go in summer opt for the weekdays. That said, summer’s longer hours of sunlight are when restaurants roll out their alfresco dining and you can also better experience the parks, Riverwalk and boat cruises. Just know there will be crowds. 

Spring in Chicago can be wet and rainy, but as long as you pack an umbrella or raincoat, it’s no big deal. Fall’s cool, crisp evenings and colorful foliage add a new dimension while out walking: Make sure your smartphone is charged so you can capture it through photos!

Where should I stay in Chicago?

Since most of Chicago’s attractions and must-sees are downtown or in the Loop, you’d be wise to pick a hotel there. Fortunately, this is also where most of the city’s hotels are. When you’re ready to check out another neighborhood, simply hop an “L” train (short for elevated trains as part of the Chicago Transit Authority, or CTA). 

Downtown and Loop hotels are often historic, landmark properties that boast a fun, jazzy bar, lounge or restaurant as well, which adds to the convenience. Some even offer indoor pools. 

The North Side is another hot neighborhood for boutique hotels, including neighborhoods like Wrigleyville, Andersonville and Lincoln Park. You’ll still be near cool restaurants and fun boutiques, as well as Wrigley Field or the Lincoln Park Zoo. Similarly, Chicago’s South Side has opened a few boutique hotels in recent years, providing a glimpse into a neighborhood that’s more laid-back and residential than downtown or the Loop, and offers a few places to visit, including the University of Chicago’s archeology and art museums and, soon, the Obama Presidential Library.  

It might be tempting to find a hotel near either O’Hare or Midway but these two locations aren’t really near attractions, and they’re quite far from downtown and the Loop. Consider spending a night near there if you have a late or early flight, but then choose a different hotel for the rest of your trip.

What are the best annual events in Chicago?

You’ll find that most Chicago festivals and events — especially those outdoors and in neighborhoods — are wedged between Memorial Day and Labor Day, because that’s when weather is the best. This includes the Chicago Blues Festival in early June and Lollapalooza in early August. One of the country’s largest Pride Parades is hosted on the last Sunday in late June. 

However, some of the biggie annual events fall outside of those dates.

This includes Taste of Chicago and Printer’s Row Book Fair, both held in early September. Another of Chicago’s most popular festivals is the St. Patrick’s Day Parade, paired with the annual dyeing of the Chicago River to an emerald-green hue.

During the summer months, fireworks kick off from Navy Pier Wednesday and Saturday evenings, and Millennium Park’s Frank Gehry-designed Jay Pritzker Pavilion hosts free outdoor classical-music concerts through its Summer Music Series Monday and Thursday nights.

Then, in winter, Zoolights at Lincoln Park Zoo and ice skating in Millennium Park are good reasons to brave the chill, while the Chicago Auto Show in February draws crowds.

Whenever you visit, there’s sure to be an exciting event happening.

What food is unique to Chicago?

Chicago is a foodie city, with its own riffs on classic foods, whether you’re ordering a Chicago-style dog from an outdoor stand or cozying up in a booth for Chicago-style, deep-dish pizza.

The brownie was actually invented in Chicago by Bertha Palmer, the wife of Palmer House Hilton’s founder, for the Columbian Exposition World’s Fair in 1893. Today you can order it, in many variations, at the historic hotel in the Loop. 

Due to “The Bear,” a TV drama on Hulu about a family-owned restaurant, Italian hot beef is back in vogue and there are many spots to sample it while in Chicago.

To further explore Chicago’s culinary scene, head to the following neighborhoods:

  • Dim sum and tea in Chinatown
  • Late-night tacos and other Mexican eats in Pilsen
  • Indian and Nepalese food along Devon Avenue
  • Bavarian-style bakeries in Lincoln Square
  • Polish and Ukrainian borscht in Ukrainian Village
  • Soul food on the South Side

What should I do on my first trip to Chicago?

Chicago literally covers every topic and interest when it comes to travel, including professional-sports teams (whether it’s the MLB, NBA, NHL, or NFL), museums, the outdoors, arts and architecture, history, food, and family travel. 

How to spend your time during your first trip in Chicago depends on what you like to do. Check off some of the highlights, including walking along the Riverwalk and onto a beach, while also admiring gorgeous architecture from the 19th century to today.

If you want to check all the most famous spots off your bucket list, spend time in what locals call The Loop by visiting a major cultural institution like the Art Institute of Chicago or the Chicago Cultural Center.

Broadway-style musicals are in downtown Chicago and running almost every night, as well as playhouses like the Goodman Theatre or Lookingglass Theatre Company. Many of Hollywood’s stars got their start on a Chicago stage: you just might see the next Academy Award winner. If you can’t get enough of comedy, Second City Chicago’s improvisational-style skits will have you howling. 

Be sure to visit at least one neighborhood outside of downtown Chicago, the Loop, or River North. Chicago is a city of neighborhoods, and it shows. You’ll be surprised at the vibrancy and authenticity in a different culture, whether it’s Pilsen’s Mexican population, the Chinese-American residents of Chinatown or Bronzeville’s African-American community. These neighborhoods offer dining, museums and shopping.

Think of your Chicago trip as a teaser for a future trip. You can’t do everything in one trip, so why even try? Simply pick a few sites and activities and enjoy!

How much time should I spend in Chicago?

While the footprint of Chicago might seem sprawling, most of what you want to see is in the Loop, downtown or otherwise near Lake Michigan, whether you’re in Lincoln Park or on the South Side. 

It helps that public transportation here is efficient, meaning you won’t be stuck in traffic. We recommend a minimum of three nights and ideally four nights in order to get the best possible experience.

What are the best transportation options in Chicago?

The good news is that you don’t need to rent a car. Chicago’s public-transportation system consists of buses and elevated trains. You can also scoot out to the suburbs on a Metra line. 

Car-share services like Lyft and Uber are also at the ready, and plenty of bike-share and scooter-rental services are throughout the city.

Where is the best shopping in Chicago?

It used to be that Chicago’s best shopping relied solely on North Michigan Avenue but that is no longer the case. 

If scoring a Burberry trench or ducking into Nordstrom isn’t your thing, check out a cute cluster of indie-owned boutiques along Armitage Avenue in Lincoln Park. Fulton Street Market, just west of downtown Chicago, is another great spot for apparel, art and gifts, and where you’re more likely to find homegrown brands. The same goes for Wicker Park, Bucktown, and Lincoln Square.