Fitness-friendly vacation rentals in South Loop, Chicago

Find and book unique fitness-friendly rentals on Airbnb

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

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

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Guest favorite

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$44,674 GYD per night

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 70 reviews

Cozy Eco-Friendly 2BD Lake Suite Near Downtown

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

Jan 21 – 28

G$32,195 GYD per night

Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 68 reviews

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

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Jul 4 – 11

G$31,105 GYD per night

Guest favorite

Apartment in Uptown

5.0 out of 5 average rating, 12 reviews

Majestic Modern Style Loft Montrose Beach WFH Gym

*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart TV, and a dedicated workstation, ideal for traveling professionals or remote workers. Unwind in comfort with an in-unit washer/dryer, dishwasher, and access to a rooftop area for breathtaking city views. Stay in shape with a fitness center. Steps away from Montrose Beach, Aragon Ballroom, and Riviera Theatre, you can balance tranquility and urban exploration. Parking available.

Jan 9 – 16

G$18,124 GYD per night

Guest favorite

Condo in Chicago

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.

Sep 24 – Oct 1

G$31,530 GYD per night

Guest favorite

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

Guest favorite

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.

Jan 7 – 14

G$27,142 GYD per night

Superhost

Apartment in Chicago

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

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Luxéry Stay South Loop - McCormick/Wintrust Area

Staying in one of Chicago's Historical Buildings, you can now experience living in the famous South Loop neighborhood conveniently located across from McCormick Place! South loop has a teeming restaurant scene with front row access to Grant Park, the lakefront Museum Campus and Soldier Field! this area is unmatched by most urban neighborhoods. Explore the celebrated jazz clubs, and other historic areas like industrial Motor Row and the charming Prairie Avenue District.

Nov 26 – Dec 3

G$61,889 GYD per night

Superhost

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

Guest favorite

Apartment in Near South Side

4.76 out of 5 average rating, 17 reviews

McCormick Oasis Balcony/Parking/Patio/Gym/sleeps 6

• MESSAGE US for SPECIAL RATES • McCormick Place only 9 min walking distance • Access to the Gym • Private balcony • 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 • Fully equipped & stocked kitchen • Minutes to all touristic destinations • Optional Parking for only $30/day

Jan 12 – 19

G$23,639 GYD per night

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 80 reviews

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

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Jun 4 – 11

G$66,226 GYD per night