Vacation rentals with a pool in West Loop, Chicago

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Top-rated rentals with a pool in West Loop, Chicago

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Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 465 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$66,220 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 190 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace with 360 degree vi

Mar 7 – 14

G$106,073 GYD per night

Superhost

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!

Jul 15 – 22

G$86,288 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!!!

Jan 18 – 25

G$32,645 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

The Downtown Oasis (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.

Feb 10 – 17

G$66,250 GYD per night

Superhost

Condo in Chicago

4.74 out of 5 average rating, 147 reviews

Central Downtown Location-Modern 2BR Condo

Newly remodeled, spacious 2 BD condo at a premiere downtown location, right by Chicago Riverwalk, City Winery, Michigan Ave & walking distance to all main attractions Chicago offers to its visitors & residents. Condo is a block away from all major L trains, including the Airport connections & convention centers, 5 min cab ride to Metra train station. Indoor pool (open year long) grill area, security & everything you would wish to enjoy your stay, will be a part of your unforgettable experience!

Jul 4 – 11

G$73,631 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

Luxury Designer Penthouse South |Pool| Gold Coast

NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Oct 23 – 30

G$140,200 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym

Feel at Home, Unwind, and Enjoy the amenities you deserve at our 3-bed 2-Story Penthouse. Guests love staying with us because: -Central location near Grant Park, Soldier Field, Art Institute, & Museums! -1 Free parking pass -FAST WIFI -En-suite Laundry -The Lake & Park are 2 blocks away -2 KING beds + 1 Queen bed -Private Rooftop Deck w/ stunning views -Amenity Floor (Gym, Pool - Temporarily Closed, Lounge, Doggy Park) -1 block from Red "L" subway This is rated the top 5 Airbnbs in Chicago.

Jul 2 – 9

G$128,176 GYD per night

Guest favorite

Apartment in Logan Square

4.97 out of 5 average rating, 58 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Oct 10 – 17

G$73,276 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 9 reviews

STUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING

Luxurious Chicago apartment in the vibrant Fulton Market District/West Loop. Private high-rise unit in a modern building, moments from top dining (Girl and the Goat, Au Cheval), Willis/Sears Tower, art galleries, trendy clubs, Whole Foods, Mary Bartelme Park, and cafes. Swift access to O'Hare Airport, Navy Pier Ferris Wheel, the Loop, Millennium Park (The Bean), Mag Mile, Lincoln Park, McCormick Place via transit. Parking included. Experience effortless, secure living in the West Loop!

Sep 30 – Oct 7

G$156,643 GYD per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 8 reviews

Cozy studio near Michigan lake

Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming studio apartment offers a delightful blend of modern comfort and vibrant city living. The decor is welcoming and will create a pleasant atmosphere. Kitchen provides everything you need to prepare meals! Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, a variety of dining options!

Jun 30 – Jul 7

G$26,191 GYD per night

Guest favorite

Apartment in Chicago

4.93 out of 5 average rating, 61 reviews

50th Floor Mag Mile Studio

This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.

Nov 5 – 12

G$62,581 GYD per night