Vacation rentals with a pool in Chicago Loop

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chicago Loop

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 462 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”

Nov 30 – Dec 7

$383 per night

Superhost

Apartment in The Loop

4.78 out of 5 average rating, 156 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, tall ceilings, and oversized windows, this spacious unit 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 views of the skyline and

Feb 5 – 12

$257 per night

Guest favorite

Condo in Evanston

4.91 out of 5 average rating, 102 reviews

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

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Heart of Evanston Condo features granite countertops in the kitchens, 9 foot ceilings and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

Dec 9 – 16

$188 per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 54 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 1 – 8

$215 per night

Superhost

Apartment in Chicago

4.93 out of 5 average rating, 28 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 13 – 20

$138 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 20 reviews

River View Cityscape Condo

Our luxurious condo has everything you need for your Chicago trip. The unit amenities come with a full gym, outdoor lounge, dedicated workspaces, and more. The condo comes complete with an in-unit washer and dryer, and beautiful city and river views. You can also enjoy using our convenient hot tub, pool, and outdoor fire pits between our seasonal months of June & September. Our Airbnb is walking distance to several popular restaurants, bars, and coffee shops. An ideal base to explore Chicago.

Jul 9 – 16

$302 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 5 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

$572 per night

Guest favorite

Condo in Lisle

4.95 out of 5 average rating, 41 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 12 – 19

$69 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 9 reviews

Lake, City, & River View Condo

Enjoy a delightful stay in my bright, stylish, centrally-located studio apartment for your Chicago trip. The unit is equipped with an indoor hot tub (open year-round), an outdoor pool (open during summer), and a dedicated workspace to make your stay comfortable. You can always enjoy using the gym, terrace, rooftop space, game room, and more. Our apartment is less than 10 min away from restaurants, The River Walk, Navy Pier, cafes, bars, nightclubs, and more. We look forward to hosting you!

May 6 – 13

$327 per night

Guest favorite

Apartment in Chicago

4.86 out of 5 average rating, 155 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!

Oct 4 – 11

$353 per night

Guest favorite

Apartment in The Loop

5.0 out of 5 average rating, 8 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!

Feb 12 – 19

$552 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 7 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!

Jul 9 – 16

$113 per night