Fitness-friendly vacation rentals in Grant Park, Chicago

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Top-rated fitness-friendly rentals in Grant Park, Chicago

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Guest favorite

Rental unit in Uptown

4.89 out of 5 average rating, 494 reviews

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

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Guest favorite

Rental unit in Irving Park

4.97 out of 5 average rating, 143 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!

Guest favorite

Condo in Lake View

4.99 out of 5 average rating, 127 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Boys Town/Wrigley Field -Newly renovated/brand new in safe centrally located East Lakeview. -10 min walk from Wrigley Field, Boys town, beaches, super markets restaurants with late night dining. 5 min walk to the Metro Sheridan Red Line (straight shot downtown), enclosed parking plus free permitted street parking, Private gym access 24/7 next door! -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish furnishings & washer/dryer!

Guest favorite

Cabin in McHenry

4.93 out of 5 average rating, 121 reviews

Riverside Retreat : A Nature Lover’s Dream!

Immerse yourself in nature at this enchanting 3bedroom cabin! Discover adventure-ready luxury in our historic 1950s riverside home. Unwind in the outdoor spa tub or challenge friends in the game room. Your gateway to riverside bliss with a private boat dock. Bring water toys and enjoy access to the Chain of lakes. Explore Moraine State Park's outdoor wonders just steps away. Indulge in downtown McHenry's dining and nightlife options. Escape to perfection in this one-of-a-kind handcrafted cabin.

Guest favorite

Home in North Park

4.96 out of 5 average rating, 150 reviews

Chicago Modern 2 bed with cool 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. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and illuminating seats

Guest favorite

Condo in Humboldt Park

4.96 out of 5 average rating, 138 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.

Superhost

Guest suite in Lake View

4.85 out of 5 average rating, 239 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

Guest favorite

Rental unit in Avondale

4.97 out of 5 average rating, 194 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.

Superhost

Rental unit in Uptown

4.83 out of 5 average rating, 143 reviews

Fabulous Uptown Apartment - Clean & Close to Train

Welcome to this beautifully renovated studio 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.

Guest favorite

Condo in Near South Side

4.87 out of 5 average rating, 143 reviews

McCormick 2B/2Ba for up to 8 guests w Opt Parking

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed + queen sized air mattress for 4 extra guests • Comfortable stay for up to 8 guests at a time • Access to the Gym • Fast Internet • 4K smart HDTV(Netflix) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Superhost

Condo in The Loop

4.84 out of 5 average rating, 117 reviews

Downtown Mich Ave #7|Safe Park 2bd Penthouse|+gym

Feel at Home and Unwind 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 beds -1 closed & 1 loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Guest favorite

Home in Lake View

4.94 out of 5 average rating, 178 reviews

Wrigleyville Greystone

First floor guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line station. Open floor plan with full kitchen, DR, double LR with 55” TV & foosball table, 3 bedrooms with queen size beds, 2 full bathrooms with bidet toilet, exercise room & back patio with sofas, table & koi pond. Since we live here and have another guests house in the building, we do not allow parties or large groups.