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Fitness-friendly vacation rentals in South Side

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in South Side

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, 141 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 24 – Oct 1

G$32,441 GYD per night

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

Aug 15 – 22

G$45,020 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 16 – 23

G$46,706 GYD per night

Apartment in Chicago

4.94 out of 5 average rating, 66 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$31,133 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.

Aug 22 – 29

G$30,960 GYD per night

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 3 – 10

G$32,325 GYD per night

Condo in Chicago

4.9 out of 5 average rating, 168 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 11 – 18

G$107,028 GYD per night

Apartment in Chicago

4.87 out of 5 average rating, 106 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!

Jun 28 – Jul 5

G$77,851 GYD per night

Condo in Lisle

4.95 out of 5 average rating, 43 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.

Mar 25 – Apr 1

G$16,474 GYD per night

Apartment in Chicago

4.87 out of 5 average rating, 156 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!

Nov 15 – 22

G$84,299 GYD per night

Condo in Portage

4.96 out of 5 average rating, 78 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Come stay at this adorable one bedroom condo on the Marina near Lake Michigan! This condo has everything you need to enjoy a special getaway from everyday life. Conveniently located near the Indiana Dunes with the South Shoreline to Chicago directly across the street. Relax on the patio and enjoy watching the boats come and go as they please. Check out the drinks and food at the Marina Shores Yacht Club just a short walk away from this unit. This condo has everything you're looking for!

Mar 27 – Apr 3

G$27,248 GYD per night

Apartment in Chicago

4.81 out of 5 average rating, 26 reviews

McCormick 2B/2Ba for up to 6 guests w Skyline view

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed for 2 extra guests • City skyline view • Comfortable stay for up to 6 guests at a time • Access to the Gym in the building • 4K smart HDTVs in ALL ROOMS(Netflix) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Jan 3 – 10

G$23,831 GYD per night

Vacation rentals for every style

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Popular amenities for South Side fitness-friendly rentals

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

Apartment in Chicago

4.97 out of 5 average rating, 178 reviews

5* City Oasis: Logan Square/Avondale Neighborhood

Sep 23 – 30

G$35,697 GYD per night

Apartment in Chicago

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Oct 5 – 12

G$26,678 GYD per night

Apartment in Chicago

4.91 out of 5 average rating, 32 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Nov 25 – Dec 2

G$32,907 GYD per night

Apartment in Chicago

4.81 out of 5 average rating, 16 reviews

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

Jan 6 – 13

G$23,661 GYD per night

Apartment in Oak Park

4.94 out of 5 average rating, 32 reviews

2BR/2BA Oak Park Gem - Ideal Comfort

Nov 26 – Dec 3

G$36,465 GYD per night

Apartment in Chicago

5.0 out of 5 average rating, 6 reviews

Luxéry Stay South Loop - McCormick/Wintrust Area

Nov 12 – 19

G$68,996 GYD per night

Apartment in Chicago

5.0 out of 5 average rating, 4 reviews

Fantastic West Loop 2 bedroom

Nov 11 – 18

G$72,307 GYD per night

Apartment in Chicago

4.95 out of 5 average rating, 57 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Sep 2 – 9

G$61,702 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 2 – 9

G$25,471 GYD per night

Condo in Chicago

4.98 out of 5 average rating, 255 reviews

Northside Chicago Favorite with parking!

Nov 30 – Dec 7

G$56,224 GYD per night

Condo in Evanston

4.91 out of 5 average rating, 102 reviews

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

Dec 2 – 9

G$45,223 GYD per night

Condo in Chicago

4.74 out of 5 average rating, 147 reviews

Central Downtown Location-Modern 2BR Condo

Jul 4 – 11

G$73,738 GYD per night

Condo in Portage

4.94 out of 5 average rating, 68 reviews

Unsalted Stay - Waterfront Condo

Oct 14 – 21

G$32,551 GYD per night

Condo in Chicago

4.96 out of 5 average rating, 56 reviews

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

Jul 22 – 29

G$111,880 GYD per night

Condo in Chicago

5.0 out of 5 average rating, 6 reviews

Downtown Park #8 Mich Ave PH - Rooftop & Gym

Jul 7 – 14

G$74,364 GYD per night

Condo in Chicago

4.99 out of 5 average rating, 81 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

Feb 10 – 17

G$48,065 GYD per night

Fitness-friendly house rentals

Home in Manteno

4.95 out of 5 average rating, 172 reviews

Manteno Luxury Comfy Cozy home with- 2 king beds!

Jan 17 – 24

G$32,659 GYD per night

Home in Chicago

4.96 out of 5 average rating, 128 reviews

Chicago Riverhouse summer on our patio!

Mar 13 – 20

G$73,024 GYD per night

Home in Chicago

4.95 out of 5 average rating, 153 reviews

Wrigleyville Private Guesthouse

Oct 31 – Nov 7

G$71,889 GYD per night

Home in Chicago

4.9 out of 5 average rating, 160 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Jul 23 – 30

G$185,500 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

Nov 17 – 24

G$46,850 GYD per night

Home in Berwyn

4.95 out of 5 average rating, 63 reviews

Beautiful 4 bedroom 3 full bath Bungalow

Nov 15 – 22

G$63,025 GYD per night

Home in Homewood

4.88 out of 5 average rating, 8 reviews

Horizon - 4 BRs, 2 BA Game Room & Gym

Oct 13 – 20

G$54,577 GYD per night

Home in Chicago

5.0 out of 5 average rating, 4 reviews

5BR/5BA Architectural Estate-Theatre, Gym, Rooftop

Apr 11 – 18

G$126,141 GYD per night

Destinations to explore