Sightseeing Tours in Chicago

Best Chicago Tours & Sightseeing

There’s no shortage of tour options in Chicago, with tours available for nearly any combination of interest, budget, mode of transport, and length of time. While most everyone knows about the boat tours of the Chicago River and Lake Michigan, the bike and segway tours of the city, and the open-topped double-decker bus tours, there are plenty of lesser-known tours of the city available. Here are a few of these smaller, more niche-focused tours. When it comes to touring Chicago, you have multiple options: bus, boat, bike, foot, or Segway.

Chicago Bus Tours

The Chicago Trolley and Double-Decker Co. operate hop-on, hop-off double-decker bus tours of Chicago. The Signature Tour package costs $26 from 9 am to 6 pm (until 8 pm in summer) with buses running approximately every 15 minutes.

Chicago Bus Tours
Chicago Bus Tours

The bus stops at the Hancock Center, River North, Water Tower, Navy Pier, Magnificent Mile, Michigan Avenue Bridge, Theatre District, Willis Tower Skydeck, Millennium Park, Art Institute, Shedd Aquarium, and Field Museum.

Along the way, passengers will learn all about the history of Chicago and the sights they’ll be visiting. The best part is that when you want to stop and explore an area or visit an attraction, you can just hop off and then hop back on the next bus when you are done. In addition to the Signature Tour, the company also offers specific neighborhood tours for a more in-depth look at the city.

Chicago Boat Tours

One of the best tours in Chicago is the Chicago Architecture Foundation River Cruise. Run by actual docents from the Chicago Architecture Foundation, these tours are packed with information and still totally entertaining. Even locals rave about this tour because they learn new facts about Chicago every time they take it. The tours last about an hour and cost $32 for adults. The tour is offered from May to November and can be booked online in advance (highly recommended on weekends and during peak summer months). The cruise passes over 50 notable buildings and sights in Chicago, with full narration from the tour docents along the way.

Shoreline sightseeing also offers 30-minute tours of the Lake from April to October. Adult prices range from $14-17 per person.

Chicago Bike Tours

Get some exercise while you see the city on a Bike Chicago bike tour. Pedal in the steps of President Obama, cruise along the Lakefront or through Chicago’s parks or visit one of the city’s great neighborhoods. Prices range from $25-$35 for adults.

Chicago Segway Tours

There are multiple Segway tour companies, but one of the most popular is City Segway Tours. The tour stops at the Field Museum, Adler Planetarium, Grant Park, Millennium Park, Soldier Field, and Shedd Aquarium,  and takes in the city skyline from the Lakefront. The cost is $70 per person and you can reserve online. The tour may be worth it for those who really want to ride a Segway, who want a quick overview of the city, or who have problems getting around but still want to see the city by foot. But if you have more time or actually plan to visit any of the stops on the tour, it’s better to skip this one and see these sights on your own.

Chicago Walking Tours

For those who prefer to take in the sights while exploring the city by foot, the Chicago Architecture Foundation also offers a variety of walking tours that are available all year round. Most take about two hours and cost $15. Walk Chicago Tours offers private and customizable tours of art, architecture, history, and culture, ranging from $20-$35 per adult. Foodies can even take a Chicago Food Tours walking tour that stops for tastes at multiple restaurants.

Chicago Foodie tours

Second City Pizza Tours

Deep-dish pizza is a staple of the Chicago diet….well, the term diet being used loosely, seeing as a single slice of deep-dish pizza can have more than 800 calories! If you’re ready to indulge and want to sample deep-dish pizza at several of Chicago’s best locations, join this tour, which stops at five restaurants. Guests get a slice at each one (that’s five slices!) while learning about the history of this unique Chicago food.  Tours are 2.5 hours and cost $36 for adults.

Vienna Beef Factory Tours

Another Chicago food staple, the Chicago-style hot dog, isn’t complete without a Vienna Beef hot dog between the bun. To see how these prized sausages are made, make reservations (far in advance) for the Vienna Beef factory tour. Tours are free and offered on Wednesdays at 10 am and 11 am, but they fill up far in advance, so make your plans early.

Chicago Dine-Around

For $85, guests on the Chicago Dine-Around tour receive a full meal over the course of several hours. Appetizers are served at the first stop, followed by the main course and dessert at two additional stops. Alcohol is not included.

Chicago Food Planet

Chicago Food Planet tours focus on some of Chicago’s distinctive neighborhoods, like Near North, Bucktown, and Wicker Park. Tours last 3 hours, cost $42 each, and include seven stops at some of the ‘hood’s best restaurants.

Chicago Chocolate Tours

Chicago Chocolate Tours visit some of the city’s tastiest bakeries and sweet shops. Tours cost $40, last about 3 hours, and visit chocolate shops in Lakeview, South Loop, and the Magnificent Mile.

Chicago Weird and scary tours

Weird Chicago Tours

Visiting Chicago’s haunted locations, crime spots, and weird places, Chicago Weird Tours cost $30 and last 3 hours. Specialized tours are also available, including serial killer tours, red-light district tours, gangster tours, and “Devil in the White City” tours.

Untouchables Tour

The Untouchables tour explores Chicago’s gangster history, providing both entertainment and information about some of Chicago’s most notorious bad boys. Tours are about 2 hours and cost $28.

Musical tours

Chicago Blues Tour

The Chicago Blues Tour offers a Blues Shuttle, which includes transportation and all admissions to 3 clubs, as well as 2 drinks and a free collection of Chicago Blues Records downloads. Offered Thursday through Sunday evenings, the private tour requires an advance reservation of 14 days and a minimum of 5 persons. Prices start at $75 per person.

Chicago Historical tours and neighborhood tours

Boystown Tour

Chicago Elevated offers a walking tour of Lakeviews’s “gayborhood,” the area along Halsted known as Boystown. Learn about the history of the area and check out some of the wonderful gay-owned and gay-friendly restaurants, bars, shops and other businesses. Tours are about 90 minutes and cost $20.

Board of Trade Tour

Want to feel like Ferris Bueller, watching the action on the trading floor at the Chicago Board of Trade? The only way to do it is with the Chicago Architecture Foundation Board of Trade tour, which takes you through the lobby and up to the observation deck. The one hour tour costs $10 and no does not require reservations.

Women of Influence Cemetery Tour

Celebrate the influential women who help shape Chicago. The Graceland Cemetery tour explores the lives of women like early settlers Juliette Kinzie and Mary Jane Richardson Jones, an African-American pioneer in civil rights; social reform leader Louise deKoven Bowen, one of the guiding forces behind Jane Addams’ Hull House; and Ruth Page and Marion Mahony Griffin, advocates for art and culture. The tour is $15 and lasts 2 hours.

Federal Reserve Money Museum Tour

Guided tours of Chicago’s Federal Reserve Money Museum last about 45 minutes and are available at 1 p.m. Monday through Friday. Tours include a guided walk through the museum, a short video about the operations of the Chicago Fed, and a Q&A session afterwards.

Chicago Film Tour

Another option for a bus tour is the Chicago Film Tour, which showcases sight used in various movies filmed in the city, and offers a full history of cinema in Chicago. The tour is perfect for film buffs who want to see a lot of Chicago in a short time, or anyone looking for a more unique way to explore Chicago.

Most people know that certain films – The Dark Knight, Blues Brothers, Adventures in Babysitting – were filmed in Chicago. But there hundreds of others that are lesser-known, and the city has a long history with feature films, dating as far back as 1910.

For a unique tour of the city that combines traditional sightseeing with entertainment and film history, check out the Chicago Film Tour.

The Chicago Film Tour departs from the Rock n’ Roll McDonald’s  (seen in the film Eagle Eye) Thursday through Sunday at 10:30 am and 12:30 pm. The two-hour tour passes by over 30 sites used in about 50 movies. It runs from downtown up to Uptown and then backs down to Chinatown, so it’s a great way to cover lots of ground and see the majority of the city in a small amount of time.

Each bus only holds 45 people; some of the streets require a smaller vehicle, so you don’t feel as though you are on a large tour bus. The buses have bathrooms and passengers are allowed to bring on any food and drink they want – yes, including alcohol. Each bus is also equipped with tv monitors, a feature that really increases the quality of the tour. You see, as the bus passes each location, the guide will play a short film clip featuring that site. One of the best parts of the tour is the chance to see the location portrayed on film and then compare it to the real thing.

Some of the sites visited include Hotel 71 (site of Bruce Wayne’s penthouse in The Dark Knight), the Biograph Theatre (where John Dillinger was shot in Public Enemies), Emmit’s Pub (used in Ocean’s 11), and the Ambassador East Hotel (filmed in North by Northwest and No Mercy, among others).

While the tour is ideal for tourists, it’s also entertaining and information for residents as well. Though I’ve been living in the city for several years, I had no idea that so many movies – the tour covers about 70 – were filmed here, including some of the early silent films. Many of these, including some with Charlie Chaplin, was filmed at Essenay Studios, which is now St. Augustine College on the city’s north side. I also learned a lot of trivia about the city, even some that weren’t strictly film-related.

Beyond serving as a set for movies, the city is tied to the film industry in many ways. Walt Disney was born in Chicago, what is now Universal Studios started here, Siskel and Ebert were born here, and the Oscar statuettes (along with the Emmy, Cleo and MTV awards) are produced here.

From Chinatown (where many of the scenes of Backdraft were filmed) to the Loop (setting for countless movies like the Dark Knight, Ocean’s 11, The Break-up, Ferris Bueller’s Day Off, High Fidelity, While You Were Sleeping and Stranger Than Fiction) up to the northside (where parts of Risky Business, a League of Their Own, and The Untouchables were shot), the tour covers pretty much the whole of Chicago and offers a behind the scenes glimpse of the city’s connection to Hollywood. It’s part film history class, part Chicago tour, and lots of fun.

Tickets for the tour are $30 per person.

Check out more Chicago sightseeing deals and read about unusual tours in Chicago.


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