
Fitness-friendly holiday rentals in South Side
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Top-rated fitness-friendly rentals in South Side
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Fitness-friendly apartment rentals

Skyline 2BR in South Loop Near Museums & McCormick
Milan was a great host! He was responsive and very communicative! His place was comfortable and very close to the McCormick Convention Center, which was where I was working from Friday through Tuesday. The couch was very comfortable along with the bed I slept in. His check in and out instructions were perfect. I will likely book his place next year.

Skyline view private bedroom
It was a very enjoyable stay. Thank you.

McCormick Place Studio/parking/sleeps up to 4
This was a nice convient place to stay, close to downtown. The staff were very nice, and helpful. I would stay at this place again when I come back to chicago

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.

McCormick Place Studio/parking/sleeps up to 4
I deeply enjoyed my stay, easy instructions, got the hang of the room well, cozy and nice for you or 2 people. it was very clean and the kitchen and bed area were pristine. I definitely recommend.

Sentral 2 Bedroom Apt in South Loop Chicago
Very easy for a local who needed a different place to stay during a remodel

McCormick 2B/2Ba corner unit/opt parking/sleeps 6
I came for the Beyoncé concert and the place was pristine. It was kind of a perfect storm of things.

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 apartment 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 (:

2BD Central Downtown Location! Spacious & Cozy
We were very happy with the Apartment, it was clean and perfect size for 4 people. Ana was super helpful and responded immediately, we loved talking to her 😄 For me due to Images, and wrong adress on the public profile, there has been some confusion about the location of the Apartment. All in all: The views are not stunning, but the location is perfect for sightseeing (and price was great location wise)! 😉

"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.
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.

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
AJ place was nothing but amazing, the pictures give you the actual home online. I wish I was able to stay longer because it’s so much to do in the home itself. I will be booking again

High End New Construction Home w/8 Beds, Parking
Great stay! The place was clean ,comfortable and exactly as described. Host was responsive and made everything easy. Would definitely stay again!

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.😜

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.
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Bed and breakfasts South Side
- Pet-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with a washing machine and dryer South Side
- Private suite rentals South Side
- Rentals with an EV charger South Side
- Rentals with pools South Side
- House rentals South Side
- Rentals with beach access South Side
- Rentals with a fireplace South Side
- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Rentals with breakfast South Side
- Family-friendly rentals South Side
- Apartment rentals South Side
- Waterfront rentals South Side
- Rentals with outdoor seating South Side
- Rentals with a firepit South Side
- Flat rentals South Side
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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
- Flossmoor Golf Club