Vacation rentals with a pool in Chicago

4.9 out of 5 average rating, 551 reviews

An indoor mosaic-tiled pool is surrounded by a spacious, elegantly arched ceiling. Soft lighting reflects off the water, enhancing the serene atmosphere. Wooden lounge chairs are placed along the poolside, providing a comfortable area to relax.

Apartment in Uptown

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”

Apartment in Fulton Market

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

4.97 out of 5 average rating, 31 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!

4.9 out of 5 average rating, 107 reviews

An outdoor pool is featured with a modern design, surrounded by grey tile and lounge chairs. Clear blue water reflects the sky above. Urban buildings rise in the background, providing a cityscape view from the pool area.

Apartment in South Loop

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.

Apartment in Printer's Row

A rooftop terrace features a sleek swimming pool surrounded by lounge chairs, with green potted plants adding a touch of nature. Expansive views of the city skyline are visible in the background, highlighting a modern high-rise building with reflective glass façades.

5 out of 5 average rating, 21 reviews

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities

Welcome to your spacious urban getaway in the heart of Chicago’s Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. Whether you're here for work or play, this retreat offers the perfect blend of style, comfort, and location. Book your stay today and experience Chicago like a local!

Apartment in Magnificent Mile

4.86 out of 5 average rating, 21 reviews

Luxury Designer Penthouse NW | 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!

Apartment in Printer's Row

An outdoor patio is presented with a panoramic view of the skyline and water. Several lounge chairs are arranged around a small table on a tiled surface, complemented by soft lighting that enhances the evening ambiance.

4.96 out of 5 average rating, 85 reviews

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

Apartment in Logan Square

4.98 out of 5 average rating, 132 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.

4.78 out of 5 average rating, 77 reviews

An inviting outdoor pool area features modern loungers and cabanas, surrounded by greenery. The heated pool reflects the skyline, while guests can be seen enjoying the space. Chic seating arrangements enhance the atmosphere of relaxation and socialization.

Apartment in River North

Level ◆ Brand New Luxe One Bedroom

Suite at Level Grand River North is the personal sanctuary that you’ve been looking for! Your modern suite is more than luxurious and spacious; they are meticulously cleaned with the highest standards for your peace of mind. A separate fee totaling $22.32 per night will be added upon arrival. This fee is separate from Airbnb and will be collected at check in. This would include a pet fee of $20 per night per pet as well as a parking charge of $68.30 per night should you choose to utilize.

Apartment in Printer's Row

A rooftop pool area is showcased, surrounded by modern skyscrapers. The pool features clean lines and metal railings, with a spacious deck made of large tiles. The backdrop highlights the city skyline under a clear blue sky.

4.9 out of 5 average rating, 30 reviews

South Loop | Rooftop With In & Out Parking | 3

Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit is perfect for corporate travelers and families looking for a chic escape in downtown Chicago 🏡💼 🔥 Rooftop Patio W/ BBQ 🍖☀️ 🏊 Rooftop Pool 🌆 🚗 Free In/Out Parking (5-Min Walk to Garage) 🅿️ 🛏️ 2 Bedrooms | 2 Bathrooms 🚿 🛌 2 Queen Beds 🛏️ 💨 1 Inflatable Airbed 🛌 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included 📺

Apartment in Chicago Loop

A refreshing outdoor pool is featured, surrounded by lounge seating and potted greenery. The pool's clear water reflects the surrounding high-rise buildings, while a gentle water feature adds a playful touch. Colorful seating options are visible in the background, enhancing the vibrant atmosphere.

4.82 out of 5 average rating, 274 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 Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

4.72 out of 5 average rating, 170 reviews

An indoor pool area is showcased, featuring sleek design elements and large windows allowing natural light to fill the space. Comfortable lounge chairs are positioned nearby, offering a serene view of the outdoors. Water flows elegantly along the pool’s edge, enhancing the tranquil atmosphere.

Apartment in Grant Park

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.