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Top Tour Operators
Bobby's Bike Hike Chicago
Sightseeing Tours, Walking Tours, Food Tours, Bike Tours, City Tours
Pizza City USA
Food Tours, City Tours, Bus Tours, Walking Tours
Spice of Life Tours
Walking Tours, Food Tours
Chicago Food Planet
Walking Tours, Beer Tastings & Tours, Food Tours, City Tours
Top Activities
Skydeck Chicago - Willis Tower
Architectural Buildings, Observation Decks & Towers, Points of Interest & Landmarks
Millennium Park
Historic Walking Areas, Parks, Points of Interest & Landmarks
Cloud Gate
Monuments & Statues, Points of Interest & Landmarks
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Bobby's Bike Hike Chicago
#1 of 132 Outdoor Activities in Chicago
So if you are able to ride a bike, enjoy being outdoors and want to see the city I would HIGHLY recommend you book a tour with Bobby's.
Even with the slight weather issue, its a good mix of indoor and outdoor.
12 Ways to experience it
Chicago’s First Lady Cruises
#2 of 132 Outdoor Activities in Chicago
It is so nice that they are finally utilizing all the space along the river for outdoor activities and dining!
Wow. Probably the best bang for your buck in Chicago if you love: outdoors; tours; history; sunshine; boats; architecture; trivia; photography; sight-seeing & education.
Chicago Running Tours & More
#3 of 132 Outdoor Activities in Chicago
At this point, I had 0 experience or interest in running outdoors.
City Running Tours-Chicago
#4 of 132 Outdoor Activities in Chicago
Free Tours by Foot
#5 of 132 Outdoor Activities in Chicago
At the end of the tour they took another 10 minutes answering our questions and guiding us where to see a magnificent Tiffany interior at the Chicago Culture Society and where do have a drink at an amazing outdoor...
tour can be taken in any weather conditions- it combines indoor and outdoor places.
Shoreline Sightseeing
#6 of 132 Outdoor Activities in Chicago
Plenty of outdoor seating and a terrific friendly staff.
The boat is all open-air and one one "floor" (e.g., there is no "indoor" lower deck and outdoor upper deck, like some boat tours have).
8 Ways to experience it
Chicago Architecture Center
#7 of 132 Outdoor Activities in Chicago
I found the outdoor views and history fascinating but the indoor stops opened up a grand view of Chicago of a hundred plus years.
Most of the tour is spent outdoors, so dress appropriately (some in our group were woefully under-dressed for the -10 C weather!).
7 Ways to experience it
Seadog Cruises
#8 of 132 Outdoor Activities in Chicago
Wendella Sightseeing Boats
#9 of 132 Outdoor Activities in Chicago
The boat was very comfortable and had indoor and outdoor seating.
This boat tour has indoor and outdoor seating.
2 Ways to experience it
Urban Kayaks
#10 of 132 Outdoor Activities in Chicago
Outdoor activity and entertaining history lesson with a great setting!
Thank you Asher, we had a blast, good job with outdoors entertaining
See it All Chicago Tours
#11 of 132 Outdoor Activities in Chicago
1 Way to experience it
Chicago Helicopter Experience
#12 of 132 Outdoor Activities in Chicago
7 Ways to experience it
Lakefront Trail
#13 of 132 Outdoor Activities in Chicago
Great for outdoor activities on summer
Whether you want to sit and watch the world go by, ride the lake side paths, swim or jog, this delightful outdoor space is an area enjoyed by all ages.
9 Ways to experience it
Tall Ship Windy
#14 of 132 Outdoor Activities in Chicago
1 Way to experience it
Wateriders
#15 of 132 Outdoor Activities in Chicago
2 Ways to experience it
Chicago Line Cruises
#16 of 132 Outdoor Activities in Chicago
2 Ways to experience it
Bike and Roll
#17 of 132 Outdoor Activities in Chicago
5 Ways to experience it
Chicago River Boat Architecture Tours
#18 of 132 Outdoor Activities in Chicago
So many outdoor restaurants and people watching as well as history and architecture.
1 Way to experience it
Mercury, Chicago's Skyline Cruiseline
#19 of 132 Outdoor Activities in Chicago
2 Ways to experience it
Lincoln Park Zoo
#20 of 132 Outdoor Activities in Chicago
You can walk around at any time of the year as there are both indoor and outdoor exhibits and events (such as markets, lectures, ice skating, etc.) From Thanksgiving until New Years Day, the park is decked in holi...
It was great outdoor activity, lots of walking and fun animals to see.Lots of Beautiful flowers
7 Ways to experience it
North Avenue Beach
#21 of 132 Outdoor Activities in Chicago
I actually like to spend time outdoors whenever possible.
5 Ways to experience it
Oak Street Beach
#22 of 132 Outdoor Activities in Chicago
Perfect for enjoying outdoor exercise and meeting people.
Great outdoor activity for the family, or alone.
2 Ways to experience it
Spirit of Chicago
#23 of 132 Outdoor Activities in Chicago
It had 3 deck levels and outdoor seating.
10 Ways to experience it
The 606
#24 of 132 Outdoor Activities in Chicago
It is a great way to see the "real city" and get some outdoor time.
3 Ways to experience it
Ohio Street Beach
#25 of 132 Outdoor Activities in Chicago
1 Way to experience it
Chica-GO Off The Beaten Path Tours
#26 of 132 Outdoor Activities in Chicago
Windy City Sailing
#27 of 132 Outdoor Activities in Chicago
Kayak Chicago
#28 of 132 Outdoor Activities in Chicago
Montrose Beach
#29 of 132 Outdoor Activities in Chicago
Chicago Electric Boat Company
#30 of 132 Outdoor Activities in Chicago