Chicago · CHICAGO LOOP & DOWNTOWN TOURS
31 tours
The Loop packs a century of architecture into eight blocks, plus a pedway system most visitors walk over without knowing. These downtown tours cover the lobbies, the plazas and the tunnels, with durations, meeting points and prices.
Chicago Loop food tour with deep-dish, Italian beef, hot dogs, sweet bites, and architecture stops, ending at Millennium Park.
“Mike was a great tour guide and the food was amazing. The route is great because it offers such a historical lesson.”
Follow Chicago’s Pedway network on a 2-hour architecture walk to City Hall, Picasso, Macy’s, and Block 37 for $35.
“Knowledgeable guide (Jessica), great pace. The pedway trip made me want to both explore the pedway system and Chicago Architecture.”
Walk Chicago’s Pedway to secret stained-glass corridors and underground pools, end near Millennium Park, and learn a transit shortcut.
“Colleen was an excellent guide and very friendly. She not only shared her knowledge on the tour, she also gave us tips for where to eat, where to go and what to do in out time in Chicago.”
Small-group Art Deco Loop walk with a Chicago Architecture Center certified guide, plus Chicago Architecture Center gallery admission.
“This tour is a must on a visit to Chicago... so much of the city's earlier 20th century history is captured in this tour of the moderne art deco architecture. One does not tend to appreciate these gems hidden among the neo-classic buildings anRead more”
Downtown Chicago Walking Pizza Tour: a small-group pizza sampler with lunch, multiple styles, and stops in River North, the Loop, and Magnificent Mile.
“Great tour John was very knowledgeable and fun guide. The pizzas we tried were all unique and tasted great.”
A 2-hour Chicago Loop walking donut tour with four classic shops, guided tastings, and real stories behind the dough.
“Our tour guide (nick) was excellent. Not only were the donuts very good (and filling - come hungry), we also got coffee and had a mini history lesson of Chicago.”
A 2-hour small-group Chicago Loop walking tour from the Cultural Center to the Marquette Building, focused on architecture and Tiffany dome.
“Guide was outstanding. Knowledgeable, proud of his city, and very friendly. I would highly recommend this tour. He runs other tours that sound great!”
Private MDW to downtown transfer with air-conditioned pickup, clear meeting steps, luggage rules, and live flight timing for $50.
“Long slow commute with a lot of traffic. Overall pleasant driver despite the time involved to get from the airport to downtown.”
Taste downtown Galena on a 5-stop small-group food and drink tour with empanadas, wine and cheese, root beer soda, Mediterranean tapas, and craft beer.
“This was such a fun experience. My husband and I enjoyed all the different stops with the owners and people. We loved the food!! ❤️ the empanadas, grilled cheese, pulled pork roll and mini doughnuts. Perfect little date adventure for a galena weekend trip!”
Taste your way through Chicago’s West Loop on a 2-hour walking donut tour with four bakeries, local stops, and a small-group guide.
“Emely is not just passionate about doughnuts, coffee, and baked goods, but also very knowledgeable about the area! Emely made it fun to walk through the streets and explore the West loop”
Small-group Loop architecture walk in Chicago with a local guide, L train rides, free building stops, and Tiffany dome views.
“Our guide was very personable, knowledgeable, and accommodating. He paced the tour in such a way that we could appreciate and enjoy the history and architectural details of the many sites we visited. He went above and beyond most guides in ensuring we had an enjoyable learning experience. I highly recommend L Stop Tours when visiting Chicago.”
A 2 hour guided walk past Chicago TV and movie landmarks, from Ferris Bueller to The Dark Knight, with expert context.
“Excellent insight to film locations and movie and tv shows past and present . Great tour would recommend.”
Kayak Lake Michigan from Ohio Street Beach by Navy Pier. Calm, skyline views, and 1 or 2 hours on the water for $39.99.
“Evan was waiting for us! He was prepared and very friendly! He really helped us and got us off on the right foot (or should I say paddle?)! We came to Evan very stressed out and left with a wonderful memory! We loved paddling around the point to see Navy Pier and then when we were returning the city scape view was stunning! We loved Kayaking in Lake Michigan! Bucket list: kayaking in Lake Michigan: check!!”
A 2-hour guided walk through downtown Chicago filming spots, from Ferris Bueller to The Dark Knight, led by actor Dan.
“Dan was an excellent tour guide and made it interesting and funny at the same time”
Kayak the Chicago River downtown for 2 hours with a paddling lesson and safety briefing. Choose single or tandem for $62.
“The person checking us in and giving us our kayaks gave the worst advice on where to kayak. Also, there were so many dead fish and birds floating and a lot of trash. My husband who ended up finishing it and going the opposite way, said it was much better and cleaner.”
