Fitness-friendly vacation rentals in Wicker Park, Chicago

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

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Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 463 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”

Aug 3 – 10

G$66,366 GYD per night

Superhost

Apartment in Chicago

4.91 out of 5 average rating, 32 reviews

Luxe Suite + Spa House Retreat! Pets Welcome

Note: New Spa House can open up to the rear yard or close up for sound insulated provacy! Indulge and recharge. Luxe 1BR + Den. Abundant east morning sunlight. Exclusivity via views of amenity yard and park beyond. Fave activities are to walk the 606 trail, BBQ and drinks on the patio, watch evening movies inside, and utilize the 24/7 access to a hot tub hydromassage in the Spa House. Be in the Logan Square 60647 zip code, enext to the 606 Trail, bring your pets, and make vacation memories!!!

Nov 25 – Dec 2

G$32,931 GYD per night

Guest favorite

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$30,983 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 3 – 10

G$32,349 GYD per night

Superhost

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$107,109 GYD per night

Superhost

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$77,910 GYD per night

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 127 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

Mar 13 – 20

G$73,079 GYD per night

Guest favorite

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$84,363 GYD per night

Guest favorite

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.

Sep 23 – 30

G$35,724 GYD per night

Guest favorite

Apartment in Chicago

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Enjoy a stylish experience at this centrally-located place. My studio apartment is right off of Lake Shore Drive. Across the street from Hollywood beach, a 4 minute walk. The 147 bus stop is right outside the apartment, which gets you downtown in 30 mins and the red line is a short 5-7 minute walk. The apartment is on the 12th floor with an amazing view of the city. The space is equipped with coffee station, records, books, art, and a great pantry of spices for those that enjoy cooking.

Oct 5 – 12

G$26,698 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 154 reviews

*Comfortable & Spacious Home Close to Downtown*

Comfortable & Spacious beautifully furnished home! 4 large bedrooms, and 3 large bathrooms. Fully equipped kitchen. This is a 2200 sq ft of a home away from home with in unit laundry. Free parking! The home is a few blocks from Humboldt Park! Blocks to the train and other nearby transportation. Easy to get a Lyft/Uber from the unit. Walking distance to restaurants, cafes and bars! Free Street parking directly in front of the building, there is no permit or parking pass needed.

Jun 29 – Jul 6

G$106,896 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 114 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.

Sep 11 – 18

G$29,511 GYD per night