
Fitness-friendly vacation rentals in Woodlawn, Chicago
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Top-rated fitness-friendly rentals in Woodlawn, Chicago
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Popular amenities for Woodlawn, Chicago fitness-friendly rentals
Fitness-friendly apartment rentals

Spacious w. Pool, gym, free gift. Sleeps 4
Thank you so much. Looking forward to staying at your place again.

McCormick Oasis 2br/2ba Parking/Patio/Gym/sleeps 6
Enjoyed my stay! Close to Solder Field and all shopping just a short Uber away. The building was very quiet and clean in a safe area. The unit was suitable for two couples or a family and was extremely excited about the coffee being available. Studebecker was readily available for my concerns and having the parking available was a great plus. I was coming to celebrate my niece graduation. Thanks for everything and would reserve again.

Skyline view private bedroom
I really enjoyed my stay here. Chandra was nice and very accommodating! She also recommended good places to visit. As a solo traveler, I felt safe and comfortable. The whole apartment was clean and I appreciated the no shoes rule. I’m definitely booking here again when I come back to this city in the future.

Level Junior Two Bedroom Suite | Fulton Market
Had such a great stay! Everything was very clean and all information given was thorough.

McCormick 2B/2Ba w opt parking for up to 6 guests
Love the location. Walking distance to everything. Starbucks around the corner. Milan was very welcoming! Definitely recommend 10/10.

Stylish Modern Retreat in Charming Mayfair
Lovely spacious apartment, we were in Chicago for the marathon and this place was perfect. Travelling downtown was really easy on the blue line. Great host and great communication, thank you!

Gym | Garage Parking | Balcony | Sleeps 6
This is a fantastic stay in Chicago! You’re within a short walk of restaurants, bars boutiques, etc. There’s a small grocery store right across the street that you can also order food at (breakfast sandwiches, etc). Great for grabbing a few essentials. The area is trendy, clean, and felt very safe. We walked downtown each day but you can also jump on the L very close by. Thomas gave very clear instructions for how to navigate the building and got back to me within minutes if I had a question. The place itself was clean and comfortable. We’re a family of four and we didn’t feel cramped. We would definitely book again!

Skyline 2BR in South Loop Chicago Near McCormick
As usually, best price/quality comparison, close to heart of downtown. Very light living room, panoramic windows with stunning view. Clean, comfortable apartment. Not first our visit and not last, fore sure. Would definitely recommend this apartment and owner!
Fitness-friendly condo rentals

2BR Apt, Office, Parking & Backyard by Wrigley
Great location to attend a Cubs game! Nice place, nice backyard to relax outside. Comfortable furniture. Fun part of Chicago for food and shopping

3 Bed Apartment in Chicago by the lake
Great, clean stay! Walkable to the lake and coffee—can’t ask for more (:

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
Will’s flat was exactly what my son and I needed on our trip to Chicago. It completely met our expectations and felt like home. My son was impressed with the comfort of the Murphy bed. The master bedroom was palatial and well-appointed. The kitchen had everything we needed, though we only used it for breakfast each day. As we were there primarily to take in a couple of baseball games we couldn’t have been happier with the location- Wrigley Field was only a few minutes away and we were close to the red line which took us to where the White Sox play. Will was very helpful with instructions and quick to respond to our questions. Absolutely would recommend this place without hesitation.

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

East Pilsen Gem
We had a wonderful time in Pilsen neighborhood. Michael & Alex are wonderful hosts and who have a beautiful home. They let us have a later check out and was very much needed after my kids being at Concert night before. No issues with communication, always very fast and clear instructions. We went to Lollapalooza and shopping. It was a little tricky figuring out the bus schedule and El, but not an issue really. They helped us with that too. We felt safe in the neighborhood and the neighbors in the building are so nice and welcoming. Parking is on the street right next to the building and never had an issue finding parking spot. Overall we had a great experience and would love to stay there again. Thank you!

Cozy 3BR on Chicago's North Side & Free Parking
This home was beautifully decorated, the beds were super comfortable, from the mattresses to the linens. We loved how clean and clearly cared for everything was, and Mark and Marcelo were responsive and helpful anytime we had a question. We needed a place that felt like home while visiting Chicago for my son's graduation, and this was perfect for the three of us. An added bonus was that there is a designated parking spot on the premises.

Logan Square Spa
This place was a total hit for our Chicago trip to see Kendrick Lamar! The infrared sauna was a hit, and the area was super chill with plenty of parking. The decor was awesome too - it was full of geeky stuff that we both loved. My partner and I were convinced the decorator could be our friend. The bookshelf downstairs had some really cool books that we didn’t even know existed. We’ll definitely check this place out again when we come back.
Fitness-friendly house rentals

Gold Coast Home|Rooftop |PoolTable |Parking |Beach
Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Rooftop Access with Views and Gym - LCP Collection
Great place in a great location. Would definitely book again!

Lakefront View Getaway Home! Hot tub! Kayak!
Hugo was a great host. The house was just like the listing, ideal for a weekend with friends. We were five couples with children, an ideal family atmosphere. It has games and equipment to enjoy the lake and garden, such as a small pool, life jackets, sport balls... It was a great weekend thanks to the space and the house, highly recommended!

Luxe King Beds-Private Gym-Huge Backyard-Crib
My daughter and I enjoyed our stay at Connor and Julie’s place. They provided a royal experience at their home. No stones were left unturned. We were able to visit the city and return back home for rest and relaxation. I highly recommend this property. It’s worth every dime. I am looking forward to returning to Chicago and staying at this property again.

Horizon - 4 BRs, 2 BA Game Room & Gym
Blaine’s place was perfect for my family! It was close to the church event that we came to participate in. The pictures were exactly as described. Plenty of space. It was very clean. The part that stood out the most to me was Blaine’s attentiveness to the one concern I had. I was having issues with the TV in the living room and reached out to Blaine. He tried to troubleshoot the problem and when he saw that did not work, he had a brand new TV and batteries delivered that night. I have stayed in several airbnbs and never experienced that level of customer service. He continued to reach out to make sure me and my families stay was a great one. Customer service is paramount! I highly recommend Blaine’s place if you are in the Chicago area!

Wrigleyville Greystone
We had a great time staying at Mark's place. We had everything we needed, close to all the things you need, easy walk to brown line and red lines to get Downtown. The space was comfortable and well decorated, with a beautiful back courtyard to hang out in. Plus if you enjoy phones, this is your kind of place.😜

Cozy 2 bedroom house/w garage in Skokie
The house is gorgeous, incredibly clean and very comfortable. Worth every cent

Andersonville Home for Groups! Hot Tub Yard Garage
We thoroughly enjoyed our stay at Josh’s place in Andersonville. It was perfect for our large gathering with the expansive and well decorated house and a backyard large enough for family lawn games. Great location for the midsummer festival in Andersonville. Very clean and comfortable beds.
Quick stats about vacation rentals that are fitness-friendly in Woodlawn, Chicago
Total rentals
10 properties
Nightly prices starting at
G$6,276 GYD before taxes and fees
Total number of reviews
340 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park