Fitness-friendly holiday rentals in West Side

Find and book unique fitness-friendly accommodation on Airbnb

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Popular amenities for West Side fitness-friendly rentals

Fitness-Friendly apartment accommodation

Superhost
Apartment in Chicago
5 out of 5 average rating, 8 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

ReginaRating, 5 stars1 week ago
Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.
Apartment in Chicago
4.9 out of 5 average rating, 221 reviews

Wicker Park - Garden At The Heart of It All

BeckyRating, 5 stars2 weeks ago
Nice place to stay in the heart of Wicker Park! Excellent off street parking. Near lots of public transit.
Apartment in Chicago
4.89 out of 5 average rating, 9 reviews

Stylish Hidden Gem in the Heart of Uptown 1BD 1BA

KierstenRating, 5 stars2 weeks ago
beautiful place in a great location
Superhost
Apartment in Chicago
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars3 weeks ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Apartment in Chicago
5 out of 5 average rating, 26 reviews

3BR Haven | Gym | Workspace | Quiet Location

AdamRating, 5 stars1 month ago
Good location, amenities, and a great experience staying here at Ella and Peter’s listing. Highly recommend!
Apartment in Chicago
4.93 out of 5 average rating, 14 reviews

Spacious Apartment Near University of Chicago

SarahRating, 5 stars6 days ago
Sheena’s place was amazing! Extremely clean, comfortable, and beautifully decorated. So many small details and amenities that are nice to have in a home when you’re traveling from out of town. We thoroughly enjoyed the movie theatre area and everyone had a space to retreat to when they needed a break from the rest of the family. Sheena also gave us a great list of ideas for places to visit and things to see while we were there. Would 1,000% recommend.
Apartment in Chicago
5 out of 5 average rating, 3 reviews

Modern 4BR: Free Pkg, Near Train & Dining

NavjotRating, 5 stars1 week ago
Charlie was great to deal with, always responsive. Clean place, easy to get in and out. They stocked a few things for breakfast which was nice. Parking wasn’t included as indicated on the initial listing but it wasn’t a big deal, there are free parking spots around.
Apartment in Chicago
5 out of 5 average rating, 9 reviews

Luxury 2BD/2BA High Rise with Views, Gym, Rooftop

ViyadaRating, 5 stars1 week ago
The unit looks better than what we’ve expected. The room is clean and neat. The apartment is also closed to the city center, which allow us to easily access many tourist attractions. Christian is also very friendly host and willing to help you out with anything.

Fitness-friendly condo rentals

Top Guest favourite
Condo in Chicago
4.95 out of 5 average rating, 59 reviews

2BR Apt, Office, Parking & Backyard by Wrigley

HeatherRating, 5 stars4 weeks ago
Great location to attend a Cubs game! Nice place, nice backyard to relax outside. Comfortable furniture. Fun part of Chicago for food and shopping
Condo in Chicago
4.76 out of 5 average rating, 33 reviews

3 Bed Apartment in Chicago by the lake

LilyRating, 5 stars2 weeks ago
Great, clean stay! Walkable to the lake and coffee—can’t ask for more (:
Top Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 stars2 days ago
Beautiful, clean unit and Will was extremely responsive and helpful. Super clean, and the beds and furniture were soooooo comfortable! It looks exactly as it does in the photos and there are so many items included, in case you forgot something! A foot massager?! Amazing 🤣The location is perfect with lots to do close by and no shortage of options for places to eat. I feel extremely fortunate that I came across this one and will definitely book again in the future. Just perfect.
Guest favourite
Condo in Chicago
4.89 out of 5 average rating, 160 reviews

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

SanjayRating, 5 stars1 month ago
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.
Guest favourite
Condo in Chicago
5 out of 5 average rating, 9 reviews

East Pilsen Gem

LisaRating, 5 stars10 months ago
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!
Top Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 287 reviews

Cozy 3BR on Chicago's North Side & Free Parking

LauraRating, 5 stars2 weeks ago
Planned a weekend trip with our daughters and their partners to Chicago. Loved this location being outside of the city but very conveniently located to public transit. The house itself was beautiful and comfortable, with plenty of room for 6 adults. A perk was the driveway parking space for our car. Would definitely recommend to others and stay again when visiting Chicago!
Condo in Chicago
4.8 out of 5 average rating, 105 reviews

Logan Square Spa

JamieRating, 5 stars1 week ago
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.
Guest favourite
Condo in Evanston
4.97 out of 5 average rating, 116 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

TaeRating, 5 stars3 weeks ago
Thanks for your kindness and support! The host and the place were amazing!!!

Fitness-Friendly Holiday House

Top Guest favourite
Home in Chicago
5 out of 5 average rating, 29 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Beach

MelissaRating, 5 stars1 week ago
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!
Superhost
Home in Oak Park
4.78 out of 5 average rating, 87 reviews

Rooftop Access with Views and Gym - LCP Collection

CynthiaRating, 5 stars2 weeks ago
Great place in a great location. Would definitely book again!
Superhost
Home in Chicago
4.86 out of 5 average rating, 56 reviews

Luxe King Beds-Private Gym-Huge Backyard-Crib

JamieRating, 5 stars4 days ago
We had a wonderful stay at this Airbnb! The house was roomy, cozy, and super comfortable. Everything was clean and beautifully decorated, with a charming backyard and deck that made it feel extra special. The bedrooms were each uniquely themed and absolutely gorgeous, and the beds were incredibly comfy—everyone slept like a dream. The water pressure in the shower was perfect, and the hosts were kind and accommodating throughout our stay. Highly recommend this place if you’re looking for a relaxing and well-kept spot to unwind!
Superhost
Home in Chicago
4.79 out of 5 average rating, 128 reviews

High End New Construction Home w/8 Beds, Parking

RebeccaRating, 5 stars1 month ago
This house was booked for a girls trip. The decorations and vibe of the house was perfect for this. It was beautiful inside and very clean. There was a small issue with getting checked in, but the hosts were very responsive so we still got in quickly.
Top Guest favourite
Home in Chicago
4.95 out of 5 average rating, 191 reviews

Wrigleyville Greystone

SheriRating, 5 stars2 days ago
The place was awesome ! We came for graduation and it worked great . Close to uber everywhere needed .
Guest favourite
Home in Skokie
4.94 out of 5 average rating, 104 reviews

Cozy 2 bedroom house/w garage in Skokie

EmanuelRating, 5 stars2 months ago
Great location, clean and most important affordable.
Top Guest favourite
Home in Chicago
5 out of 5 average rating, 20 reviews

Logan Sq/Avondale luxury chic Townhome.

SamanthaRating, 5 stars2 weeks ago
We had a wonderful stay at Rafal's place. The house we large, had many bathrooms, a nice big kitchen and an awesome deck that we spent a lot of time on. We had one minor issue pop up and Rafal was immediately responsive and remedied the situation right away. The house is in a beautiful neighborhood near many shops, restaurants and transportation. I would definitely stay with Rafal again!
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 55 reviews

Entire Luxury Home: Private Gym

MarquelleRating, 5 stars3 weeks ago
Our stay was perfect and I would definitely stay again! We hosted a small dinner for my mom’s memorial service and they were very accommodating. There was plenty of space for everyone and the location was great. All the amenities were top notch and the decor was amazing. We felt right at home and I’ve referred people to stay. Thank you so much for hosting us. 10 stars!!!

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