Chicago · TOURS
Every trip has one free afternoon too few. These 15 tours & days out justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
90-minute Chicago River architecture cruise with indoor and outdoor decks, expert narration, and standout views of the skyline’s best-known buildings.
“We had a great time. The guide we had was great and explained the history and other great information along the tour. A great way to see the city and get some history too”
Chicago Loop bootleggers, ghosts, and Al Capone lore, guided by a historian. Walk key landmarks, plus optional minibus upgrade.
“Taka was our guide and she was fantastic. We had such a good time, she was a very good story teller, loud and clear. Lots of interesting information. We learned alot and had a lot of fun.”
Ride Chicago by coach to the St. Valentine’s Day Massacre, Dillinger sites, and mob haunts. Live guide, photo stops, mini museum included.
“Incredibly interesting and such a cool tour!! Our tour director Maddie is a fantastic story teller and it was so cool to learn who all these people were. 2nd time in Chicago and learned more on this tour than anything else! Highly recommend!”
A 45-minute Chicago River architecture cruise from the Magnificent Mile, with live narration, great views, and indoor warmth options.
“This was such a fun experience even in the freezing cold! I went solo and didn’t feel out of place. The directions were clear, the tour started on time with plenty of seating and options for alcoholic/non alcoholic beverages. Great information and stunning views along the river 10/10”
A 1.5-hour Chicago architecture cruise with live narration, Lake Michigan skyline views, and river landmarks from Wendella.
“This was a great tour if you are wanting to many of the buildings and the skyline from the lake. The guide was knowledgeable with the history and construction of the buildings”
Hop-on hop-off Big Bus Chicago tour with open-top views, 11 downtown stops, and audio commentary, using a 24 to 72 hour pass.
“Big bus is not Greyline hop on hop off but did provide a great way to get an overview of Chicago downtown, parks, and museums.”
Chicago’s classic foods meet downtown landmarks on an easy 3-hour walk, with tastings included and a free bike or kayak bonus.
“The tour guide was great and since we were charged the entire fee but didn’t get to see everything without warning that booking on New Year’s Day tour one tour stop food place would be canceled. That was disappointing. But you all can use that extra we didn’t use for that place and give to our tour guide lady as her tip. She was with Gabe from Bobby bike and hike tours 11:30 tour on 1.1.2026. She was trying to be as enthusiastic and did explain as much about Chicago but we just wanted to go sit down and eat at places :) And they were nice places to stop…”
Chicago South Loop gangsters and ghosts guided walk with a historian, inside hotel stops, Riverwalk and Death Alley stories, 2 hours.
“Bailor was our guide and she’s the best! Super interesting and fun. We were happy to learn new things of Chicago.”
See Chicago’s architecture from the river on a 90-minute guided cruise, passing key towers, Chinatown, and Navy Pier, with AC and photo views.
“David was a great and knowledgeable tour guide! He gave just enough details of the skyline without being overwhelming or boring.”
Step inside Chicago’s Loop interiors on a two hour guided walk, from Art Deco Board of Trade to the Cultural Center. Small group.
“We had a great experience with Kaylee as our guide. She is well-versed in the subject and was very detailed while keeping things engaging yet entertaining.”
Chicago Loop donut walk with 5 stops, enough tastings for a sweet meal, local stories, and vegan options on request, $70 for about 2 hours.
“This tour was FANTASTIC! The guides were extremely engaging, and you learn as much about Chicago as you do about the donuts!”
Open-top Big Bus hop-on hop-off gets you quick, flexible access to Chicago’s top sights, with app tracking, digital audio, and great skyline views.
“Great! I loved this tour because it gives you the opportunity to identify key buildings and view all of downtown”
Taste Chicago classics and see major architecture fast on a small-group Loop walk with the Pedway and Millennium Park’s Bean.
“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
A 3-hour small-group Chicago Loop food walk with deep-dish pizza, dipped Italian beef, hot dogs, sweets, and major architecture stops.
“Make sure you are hungry when you arrive because there is a ton of food! The whole experience was 5 star. Lots of history mixed with great cuisine. Eliot was easy going and made the tour fun!”
Chicago mob and crime bus tour with Dillinger sites, St. Valentine's Day Massacre, and Frank Nitti museum, 90 minutes.
“Lots of information to digest. Nice being able to get off the bus. Our guide was great.”
Every kind of day out in the city, and the best of each.
