Things to do in Chicago, Illinois (IL): The Best Outdoor Activities

February 24, 2022 Vivienne Hutton

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Windy City Diving

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5.0 based on 5 reviews

Windy City Diving

Chicago's Finest Dive Charter. Whether your a beginner or a seasoned diver Windy City Diving will meet your diving needs and expectations. Captain Jim's only aim is to ensure your comfort, safety and enjoyment. Let the adventure begin.

2. Solidarity Drive

E. Solidarity Dr., Chicago, IL 60605
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75%
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25%
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5.0 based on 4 reviews

Solidarity Drive

3. New Adventure Sailing

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5.0 based on 13 reviews

New Adventure Sailing

Come Aboard “New Adventure” - Spacious cockpit has seating for six and the Captain & Crew. This luxury sailboat has two staterooms, a full sized bathroom, galley and living room with dining table. Air conditioning, TV, DVD and stereo are just some of the features to make your experience enjoyable. New Adventure is docked in Burnham Harbor, Lake Michigan (near Soldier Field). Get involved, take the wheel, help with the sails, or just sit back, relax and enjoy. Every adventure is unique, different and tailored to what you want to do: sail, anchor for a swim, or motor through the harbors. Bring your phone’s playlist and we can pipe the music up to the cockpit area. Once you book your charter, the boat is all yours - we do not combine groups.

4. The Sophisticated Lady Cruises

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5.0 based on 1 reviews

The Sophisticated Lady Cruises

Located in the heart of Chicago, the Sophisticated Lady private yacht rental offers the largest cruise vessel in the 49-passenger boat category in Chicago. For a comparable price the Sophisticated Lady offers more cabin space, deck space, total square footage than any other yacht in its class. This 72 foot Chris Craft Motor, Lake Michigan Yacht rental can carry 49 passengers in style and comfort.

5. The Salty Dog Sailing Co.

Excellent
97%
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5.0 based on 32 reviews

The Salty Dog Sailing Co.

Join us for a 2 hour private Chicago sailing charter, for groups of 2-6, departing from Burnham Harbor 5 times per day, 7 days per week. Please visit our website, call, text, or email and BOOK a Chicago sailing tour today! https://saltydogchicago.com.

6. Storm Warning Chicago Fishing Charters

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5.0 based on 5 reviews

Storm Warning Chicago Fishing Charters

Storm Warning Fishing Charters offers the best experience for your Chicago fishing charter. Enjoy your Chicago fishing trip out on Lake Michigan with our boat rentals. Trust only Storm Warning Fishing Charters for the best experience for Lake Michigan fishing charters. Contact us and book a fishing trip today!

7. ChicaGo By Boat

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5.0 based on 12 reviews

ChicaGo By Boat

ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. Whether it's your first time, only time, or just the next time--we want your sailing experience with us to be the BEST time you have this Summer.

8. Offshore312

Offshore312

From the folks at Reggies Rock Club/Music Joint comes Offshore – Chicago’s newest and best party boat charter rental! Hit the City from the water on our 37 foot Sea Ray Yacht with two bathrooms, air conditioned changing room and main cabin (inside sitting area), hot water shower, gas bbq grill, Bluetooth stereo, and room for 12 people. Take advantage of the FREE TANDEM KAYAK AND 2 PADDLEBOARDS!

9. Adelines's Sea Moose

Adelines's Sea Moose

Adeline’s Sea Moose is the perfect venue for private parties and architectural tours! There are 4 levels of expansive entertaining space both in and outdoors and our attentive and discreet crew members are on hand to cater to all of your needs! At 68 feet, Adeline boasts private panoramic views of the city and her bar & lounge open up to the elements.

10. ATGeneTravel

ATGeneTravel

We are US and China travel experts. Our office located in Chicago. We make different itineraries based on our client needed and always give the best suggestion. 我们是中美旅游专家,我们的办公室在芝加哥,根据客户的不同需要量身打造客人最满意的旅游路线。

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