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Fitness-friendly vacation rentals in West Loop, Chicago

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in West Loop, Chicago

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

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Apartment in Chicago

4.82 out of 5 average rating, 142 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

Sep 4 – 11

G$32,349 GYD per night

Apartment in Chicago

5.0 out of 5 average rating, 10 reviews

Skyline Oasis: City & Lake Views

Welcome to our breathtaking one bedroom penthouse-like corner apartment! With stunning city, lake, and river views, this high-floor oasis offers an unforgettable stay. Stylish and luxurious designer furniture, spacious balcony, full kitchen stainless steel appliances, work area, fast wifi, immaculate cleanliness, rain shower, king-size bed, TVs, fan, AC. Building amenities: pool, jacuzzi, fitness room, plus more. Cleanliness is our top priority, ensuring an immaculate space for your stay. Enjoy!

Jun 27 – Jul 4

G$87,437 GYD per night

Apartment in Chicago

4.95 out of 5 average rating, 55 reviews

The Executive's Escape (2BD/2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Jan 9 – 16

G$44,613 GYD per night

Apartment 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.

Oct 17 – 24

G$29,219 GYD per night

Condo in Humboldt Park

4.97 out of 5 average rating, 101 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Oct 2 – 9

G$31,040 GYD per night

Condo in Chicago

4.89 out of 5 average rating, 169 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!

Jul 24 – 31

G$106,931 GYD per night

Apartment 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.

Oct 26 – Nov 2

G$35,325 GYD per night

Apartment in Chicago

4.89 out of 5 average rating, 57 reviews

McCormick 2br/2ba Oasis Parking/Patio/Gym/sleeps 6

• MESSAGE US for SPECIAL RATES • McCormick Place only 9 minute walking distance • Access to the Gym • Rooftop access and Beautiful patio set up with outdoor furniture • Dedicated Internet • 4K Roku HDTVs in ALL rooms with Netflix and Roku • Queen size beds in both bedrooms + Sofa bed in the living room for 2 extra guests • Prime location with Michigan avenue crossing • Fully equipped & stocked kitchen • Minutes to all touristic destinations • Optional Parking space for only $30/day

Feb 14 – 21

G$22,789 GYD per night

Apartment in Near South Side

4.78 out of 5 average rating, 88 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 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

Jan 15 – 22

G$18,571 GYD per night

Apartment in Chicago

4.82 out of 5 average rating, 110 reviews

Charming Uptown Studio - Clean & Close to Train!

Welcome to this beautifully renovated studio 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.

Jan 24 – 31

G$29,462 GYD per night

Apartment in West Town

5.0 out of 5 average rating, 8 reviews

Lavish Apartment & City Skyline Vistas | The Jewel

Stay in our secure, luxury 1-bed 1-bath apartment in West Town, Chicago. Perfectly located off I 90/94, with easy access to ride shares. Just a 5-min walk to the Chicago Blue Line, close to United Center, Fulton Market/West Loop, River North, and Wicker Park. Enjoy nearby restaurants and stores. Garage parking available at a daily rate. Ideal for experiencing Chicago's vibrant neighborhoods and conveniences. Don't miss this prime location for your Chicago stay!

Jun 3 – 10

G$61,406 GYD per night

Apartment in Chicago

4.97 out of 5 average rating, 62 reviews

Location! Location! Location!

Keep it simple at this peaceful and centrally-located place. Only minutes from downtown Chicago by car, bus or train. McCormick Place convention center is just a little over 1 mile away. Catch some sun and have a little fun at the famous 31st Street Pier only a 10 minute walk away. Enjoy Chicago after hours nightlife in the South Loop.

Jul 5 – 12

G$28,644 GYD per night

Vacation rentals for every style

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Popular amenities for West Loop, Chicago fitness-friendly rentals

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

Apartment in Chicago

4.89 out of 5 average rating, 465 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Jul 23 – 30

G$66,255 GYD per night

Apartment in Gold Coast

4.8 out of 5 average rating, 143 reviews

Stunning Corner 2BR in Streeterville | Roof Deck |

Aug 31 – Sep 7

G$81,197 GYD per night

Apartment in Near South Side

4.79 out of 5 average rating, 19 reviews

Cozy Condo near Downtown Chicago

Jan 22 – 29

G$30,428 GYD per night

Apartment in Uptown

5.0 out of 5 average rating, 12 reviews

Majestic Modern Style Loft Montrose Beach WFH Gym

Jan 9 – 16

G$18,124 GYD per night

Apartment in Chicago

4.9 out of 5 average rating, 68 reviews

Ground-Level Speakeasy: 1BR-1.5BA Near Everything!

Jul 4 – 11

G$31,105 GYD per night

Apartment in Logan Square

4.91 out of 5 average rating, 32 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Apr 20 – 27

G$32,662 GYD per night

Apartment in Old Town

4.91 out of 5 average rating, 58 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Aug 16 – 23

G$94,094 GYD per night

Apartment in Chicago

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Oct 14 – 21

G$25,464 GYD per night

Fitness-friendly condo rentals

Condo in Evanston

4.76 out of 5 average rating, 568 reviews

Spacious Evanston Unit - Walk to Northwestern U

Dec 3 – 10

G$25,448 GYD per night

Condo in Chicago

4.74 out of 5 average rating, 147 reviews

Central Downtown Location-Modern 2BR Condo

Jul 8 – 15

G$70,609 GYD per night

Condo in Chicago

4.98 out of 5 average rating, 256 reviews

Northside Chicago Favorite with parking!

Feb 22 – Mar 1

G$49,438 GYD per night

Condo in Evanston

4.91 out of 5 average rating, 102 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Aug 12 – 19

G$73,991 GYD per night

Condo in Chicago

4.81 out of 5 average rating, 74 reviews

Logan Square Spa

Aug 19 – 26

G$38,148 GYD per night

Condo in Chicago

4.96 out of 5 average rating, 57 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Jul 4 – 11

G$109,451 GYD per night

Condo in Chicago

4.9 out of 5 average rating, 80 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Jun 4 – 11

G$66,563 GYD per night

Condo in Chicago

4.99 out of 5 average rating, 83 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

Apr 27 – May 4

G$48,871 GYD per night

Fitness-friendly house rentals

Home in North Park

4.95 out of 5 average rating, 129 reviews

Chicago Riverhouse summer on our patio!

Dec 22 – 29

G$71,212 GYD per night

Home in Chicago

4.95 out of 5 average rating, 153 reviews

Wrigleyville Private Guesthouse

Jan 30 – Feb 6

G$71,824 GYD per night

Home in Wrigleyville

4.9 out of 5 average rating, 161 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Jul 23 – 30

G$185,332 GYD per night

Home in Des Plaines

4.83 out of 5 average rating, 167 reviews

Exotic House - Few minutes from O'Hare and Chicago

Jan 30 – Feb 6

G$45,307 GYD per night

Home in West Town

4.83 out of 5 average rating, 23 reviews

Urban Oasis: 2 floors with 2 bd/2ba and backyard

May 24 – 31

G$75,658 GYD per night

Home in Skokie

4.94 out of 5 average rating, 83 reviews

Cozy 2 bedroom house/w garage in Skokie

Apr 3 – 10

G$53,419 GYD per night

Home in Berwyn

4.95 out of 5 average rating, 63 reviews

Beautiful 4 bedroom 3 full bath Bungalow

Dec 23 – 30

G$74,692 GYD per night

Home in Humboldt Park

5.0 out of 5 average rating, 25 reviews

H&H 1896 - Modern/ Garden/ Free Parking/ Sleeps 21

Oct 28 – Nov 4

G$162,334 GYD per night

Quick stats about vacation rentals that are fitness-friendly in West Loop, Chicago

Total rentals
320 properties
Rentals with a pool
250 properties have a pool
Pet-friendly rentals
220 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
2.3K reviews
Nightly prices starting at
G$8,345 GYD before taxes and fees

Destinations to explore