Trip inspirationArea guideFamily friendlyQuizzes and fun
Casey Makovich

Chicago Sightseeing Tours - The Best Ways to Explore Chicago for First Timers

There's so much to do and see in Chicago that sometimes the city is best explored with a little help from professional tour guides. We put together a list of the best Chicago sightseeing tours in the city to help you choose one tailored to your interests.

Save on Popular Chicago Sightseeing Tours & More

Admission to a bunch of these attractions are included on the Go Chicago® Card. Choose as you go from dozens of top attractions and save up to 55% on combined admission vs paying at the gate. See all available Chicago passes, attractions & prices. A few of the available sightseeing activities include...

  • Hop On Hop Off Big Bus Chicago
  • Architecture River Cruise
  • Bike and Roll Chicago
  • Navy Pier Centennial Wheel
  • and more!

Hop On Hop Off Big Bus Chicago Tour

Image of Backpack, Handbag, Adult, Female, Person, Woman, Shoe, Male, Man, Bus, Vehicle, Car, People, Hat, Boarding, The Big Bus Hop-On Hop-Off Bus Tour is one of the best ways to get to know the city and start your trip before exploring on your own. This tour takes you around the city and makes stops at major attractions and landmarks where you can enjoy the flexibility to hop on or off and explore an are at your own pace. Along the way knowledgeable and friendly tour guides will fill you in on Chicago's history and culture while proving insider info, too. Highlights of the tour include: Museum Campus, Navy Pier, Water Tower Place Mall, Willis Tower, and more. Getting In: Hop On Hop Off Big Bus Chicago Tour tickets are included on the Go Chicago Card.

Architecture River Cruise

Image of City, Metropolis, Urban, Condo, Housing, High Rise, Office Building, Boat, Vehicle, Water, Waterfront, Neighborhood, Nature, Outdoors, Scenery, Cityscape, Downtown, Take a cruise along the Chicago River and learn about the city's most iconic landmarks, practically building by building, that populate the skyline as you pass by. Your guide will tell the dramatic story of Chicago’s rise from the ashes of the Great Fire of 1871 and its path to becoming known as the home of the skyscraper. Some popular sights you’ll see you on your Architecture River Cruise include buildings by Mies van der Rohe, Skidmore Owings Merrill, and Helmut Jahn, plus the Willis Tower,Old Post Office Building, and more. Getting In: Chicago Architecture Boat Tour tickets are included on the Go Chicago Card. This attraction is seasonal.

Chicago Architecture Foundation

Image of City, Metropolis, Urban, Office Building, Grass, Convention Center, High Rise, Get the full architectural history and culture experience and stop by the Chicago Architecture Foundation to join in on one of their many walking tours. Each tour focuses on a different theme and will explore varying parts of the city. At the Chicago Architecture Foundation can also take a look at the various free, informative exhibits about architectural history, contemporary developments in building standards, trends, and the modern sustainability movement. Getting In: Chicago Architecture Foundation tickets are included on the Go Chicago Card.

Chicago Theatre Tour

Image of Cinema, Person, Urban, City, Tour the iconic Chicago Theatre, recognizable as the theater featured in the hit musical Broadway, and home to legendary performances by world-class actors and actresses- a must see for history buffs and fans of Chicago's rich theater culture. You’ll get to walk across the same stage as the likes of Frank Sinatra and Dean Martin, see the walls with tons of celebrity autographs scrawled across them, and take a look at the historic photo exhibits. Getting In: Chicago Theatre Tour tickets are included with the Go Chicago Card.

Historic Chicago South Shore Tour

Image of Person, Postal Office, City, Urban,

This 2-hour tour, comprehensive Gray Line tour of Chicago’s South Shore is a great way to learn about some of the most iconic architectural and historical sites of Chicago’s South Shore along with some of the highlights of Chicago you might not otherwise visit. The fully narrated tour begins in the iconic Grant Park near the Art Institute of Chicago, and continues south towards the Museum Campus, Solider Field (home of the Chicago Bears), then down on to Jackson Park and beyond.
Getting In: Historic Chicago South Shore Tour tickets are included on the Go Chicago Card.

Panoramic and Scenic North Side Tour

Image of City, Urban, Cityscape, High Rise, Nature, Outdoors, Scenery, Metropolis, Downtown, Landscape,

This 2-hour Gray Line tour of Chicago’s North Side is a takes you through downtown Chicago and to North Side attractions. If you're looking to see Wrigley Field (where the Chicago Cubs play), the Botanical Gardens, and Lincoln Park, this is a great tour option. You’ll also get to check out some major sites of the city center, like Richard J. Daley Plaza, the Magnificent Mile, the John Hancock Tower (where 360 CHICAGO is), and Water Tower Place. You’ll travel “The Loop,” through the financial district, past some of the most famous Chicago landmarks, and continue on up to Lincoln Park. It’s a great introduction to some of the major sites in the Windy City.
Getting In: the Panoramic and Scenic North Side Tour tickets are included on the Go Chicago Card.

Grand Tour

Image of City, Nature, Outdoors, Scenery, Urban, Grass, Park, Cityscape, Downtown, Water, Waterfront, Metropolis, Person, Get the best of the two tours listed above on the 4-hour Grand Tour of Chicago that takes you to both the North Side and South Shore districts. The tour travels through Grant Park, the 'front lawn' of the city and where Soldier Field is, home to the Art Institute of Chicago and Orchestra Hall, the Museum of Science and Industry, and Lake Point Towers -- once the world's tallest apartment building -- an architecturally stunning building of glass and curves.
Tour the famous 'Loop' and State Street and journey over the Chicago River, made to flow backwards by one of the world's greatest engineering feats. All the sights covered in the North Side and South Shore tours are included in the Grand Tour and time permitting, the Grand Tour will stop to take in the breathtaking views at the Lincoln Park Conservatory and the Museum Campus. Getting In: Grand Tour tickets are included on the Go Chicago Card. This attraction is seasonal.

Bike and Roll Chicago Bike Rentals

Image of Adult, Male, Man, Person, Bicycle, Vehicle, Handbag, Shoe, Glasses, If you want to mix in a little activity to your sightseeing, head to Bike and Roll Chicago at Navy Pier to get a bike rental for the day and explore Chicago's miles upon miles of bike-friendly paths, trails, and parks. There are actually 26 full miles of lakefront trails for you to enjoy, so you’ll really be able to get a feel for the beautiful scenery (and a pretty good workout!). Getting In: Bike and Roll Chicago rentals at Navy Pier are included on the Go Chicago Card.

Navy Pier Centennial Wheel

Image of Amusement Park, Fun, Don't leave Chicago without exploring Navy Pier, one Chicago’s most-visited points of interest. As home to tons of attractions, including the Chicago Children’s Museum, Chicago Shakespeare Theater, a massive concert venue, rides, and more, you can practically spend the entire day there. One of the most popular attractions on Navy Pier is its iconic Ferris wheel, visible from many vantage points across the city. There are also a few other theme park-style rides to enjoy, from swings to a mini-golf course. Getting In: Navy Pier Centennial Wheel tickets are included on the Go Chicago Card. Although entrance to the Pier itself is free, your Go Chicago Card covers admission the Centennial Wheel and other select rides.

SkyDeck Chicago

Image of Building, Tower, Landmark, Willis Tower, The view from Skydeck Chicago (at the Willis Tower).
Make sure you spend some time sightseeing from high above Chicago, like at SkyDeck Chicago which is part of the observation deck of Willis Tower. Located on the 103rd floor, here is where you will be sure to find some of the best views of the city, spanning from Navy Pier to Soldier Field. Getting In: SkyDeck Chicago at Willis Tower tickets are included on the Go Chicago Card.


Image of City, Face, Head, Person, Selfie, Urban, Photography, Building, High Rise, T-Shirt, Adult, Female, Woman, Electronics, Mobile Phone, Phone, Portrait, Metropolis, Tourist, Vacation, Another amazing observation deck is located high up on the 94th floor of the John Hancock Building. 360 CHICAGO provides breathtaking views of Chicago’s skylines and shorelines. Located just off Magnificent Mile, this really is a must-do attraction, and a local favorite. Getting In: 360 CHICAGO tickets are included on the Go Chicago Card.

Remember to Save on Sightseeing Admission

So there you have it. Our list of some of the best Chicago sightseeing tours and other fun ways to explore this wonderful city. Remember, many (if not all) of these options are included on the Go Chicago Card, where you can save up to 55% on combined admission vs paying at the gate. We hope you plan to add a few of these fun touring options to your vacation itinerary.

Love this article? Why not share it:

Buy with confidence

Free cancellation

Plans can change, we get it. All non-activated passes are eligible for a refund within 90 days from your purchase date.

Find out more


Confused? We're here to help!

See our FAQs

We're kind of popular, but don't just take our word for it.

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.

  • Thick check Icon