Fitness-friendly holiday rentals in Chicago

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Chicago

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 121 reviews

Urban Cottage:Near Transit/20min MagMile & Wrigley

Inside a Classic Chicago brick building with high ceilings and plenty of light -centrally located for all your sightseeing needs! A well-equipped kitchen with quartz countertops and stainless steel appliances-this apartment is perfect for families and friends looking for easy access to downtown without sacrificing a neighborhood vibe. Irving Park is referred to as the "country in the city" with green spaces & tree lined streets. Plenty of restaurants & cafes nearby, we'd love to host you here!

12–19 Dec

$271 SGD per night

Superhost

Flat in Chicago

4.83 out of 5 average rating, 138 reviews

Modern, Spacious 3BR Apt Minutes to Downtown!

Enjoy a modern 3-bedroom apartment in one of Chicago's most popular and on-the-rise neighborhoods, Pilsen. TV's located in each bedroom and living room. Feel free to connect to Netflix, Disney+, Amazon Prime, etc. using your own login. A dedicated office space with a pull down bed for late night work sessions. A 10-minute Uber ride to DWTN. Just a 5-minute walk away from The Heart of Italy - CHICAGO'S ORIGINAL LITTLE ITALY Restaurants include: La Fontanella Bruna's Ristorante Bacchanalia

25 Sep – 2 Oct

$219 SGD per night

Guest favourite

Flat in Oak Park

4.88 out of 5 average rating, 104 reviews

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

19–26 Aug

$194 SGD per night

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 167 reviews

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

7–14 May

$519 SGD per night

Superhost

Flat in Chicago

4.87 out of 5 average rating, 105 reviews

Idyllic Lakefront Sanctuary W/ Unforgettable Vista

From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside of the huge windows. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances, & thoughtfully provided amenities. You will want for nothing during your stay and may not want to leave! Don't miss out on a true lakefront gem, book today!

30 Nov – 7 Dec

$410 SGD per night

Guest favourite

Apartment in Lisle

4.95 out of 5 average rating, 41 reviews

Peaceful Condo in Lisle, Illinois

Quiet condo with balcony overlocking the forest located in Lisle. Minutes from I-88, I-355, Commuter train goes directly to Chicago, Benedictine University , North Central College , Wheaton College. Shopping, movie, restaurant are walking distance. Access to pool , Lake , fishing, disc golf, canoes, tennis court, volleyball, walking paths, ski and snowboard hill, Restaurant/ pub with live music and entertainment, Convenience store. Discounts for weekly bookings longer stays over 28 days.

15–22 Oct

$110 SGD per night

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 126 reviews

Chicago Riverhouse summer on our patio!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. Amazing chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Chill private patio with illuminating sofa

7–14 Sep

$426 SGD per night

Guest favourite

Flat in Chicago

4.86 out of 5 average rating, 154 reviews

Stunning Panoramic Chicago Views & Free Parking

Indulge in the epitome of luxury at our exceptional property with a host of amenities: 24-hour door attendant, heated parking, hot tub, modern workout and rec room, and stunning Chicago views. Situated in a secure, scenic South Loop neighborhood, our upscale abode grants swift access/steps to McCormick Place and Wintrust Arena. Discover the best of Chicago from this ideal spot, with easy public transport and airport commutes. Your remarkable experience begins in this lavish urban retreat!

2–9 Nov

$561 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 178 reviews

5* City Oasis: Logan Square/Avondale Neighborhood

Indulge in our two-bedroom one-bath retreat accommodating up to 4 guests. This space goes beyond relaxation; it's a revitalizing escape, catering to both tranquility and activity with a private deck. Your comfort, ease, and well-being are our focus. This isn't just a stay; it's a realm for crafting cherished memories, unwinding in luxury, discovering new facets of the city, and thriving in every sense. Reserve now and let our haven be your canvas for an extraordinary Chicago escapade.

15–22 Sep

$238 SGD per night

Superhost

Flat in Chicago

4.79 out of 5 average rating, 66 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size Air mattress for 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

11–18 Feb

$124 SGD per night

Guest favourite

Guest suite in Chicago

4.97 out of 5 average rating, 63 reviews

Spacious, Comfy, and Private in Ravenswood Manor

Over 2,000 sq ft, this basement has 10 ft ceilings, full kitchen, bath, and makes you feel at home. With a 65” inch smart tv, washer/dryer, and internet, you have everything you need. Owners reside upstairs, but are very quiet and accommodating. Come stay in one of the best and convenient areas in Chicago. This home on on a dead end street is only 2 blocks to the brown line train which goes downtown (about 40 min ride). Restaurants and shopping at lincoln square is 15 min walk.

21–28 Apr

$202 SGD per night

Superhost

Flat in Chicago

4.87 out of 5 average rating, 112 reviews

Modern Uptown Apartment - Clean & Close to Train!

Welcome to this beautifully renovated apartment located in the Uptown neighborhood. This apartment has access to a shared fitness area, backyard/garden, and comfy work station. The building is a block from the Red Line train and is walking distance to neighborhood restaurants, bars, shops, and cafes. This apartment is perfect for remote workers or travelers looking to be in a nice neighborhood close to the city! Check in is completely contactless with a keypad & door code.

6–13 Mar

$196 SGD per night