
Home rentals with a pool near Union Park
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Top-rated rentals with a pool near Union Park
Guests agree: these stays are highly rated for location, cleanliness, and more.

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”
4.9 out of 5 average rating, 600 reviews
Professional's Playground (Fitness Center • Sauna)
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.
4.92 out of 5 average rating, 129 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!
4.98 out of 5 average rating, 40 reviews
Luxury Designer Penthouse 3803 | 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!
4.89 out of 5 average rating, 57 reviews
Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design
4.91 out of 5 average rating, 46 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.
4.98 out of 5 average rating, 172 reviews
Spectacular 2BR Penthouse in the Loop | Roof Deck
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!
4.81 out of 5 average rating, 355 reviews
Level Studio | Fulton Market
Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.
4.76 out of 5 average rating, 67 reviews
Level ◆ Brand New Luxe One Bedroom
Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.
4.79 out of 5 average rating, 163 reviews
50th Floor Mag Mile Views, Balcony, Pool, Gym
The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.
4.9 out of 5 average rating, 140 reviews
360RoofSKYview|ARTy|Garage+HotTub|EVTesla|Sleeps12
🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 🎯 Free Private Garage 🎯 Hot Tub 🎯 360° Roof Deck with Skyline + Willis Tower Views Perfect for family trips, romantic escapes, or friend getaways! ✨ Private keyless entry 🛏 Luxury KING, 2 QUEEN beds + fireplace 🍽 Full kitchen + balcony 📺 3 Smart TVs (Netflix, Disney+, Prime) 🚀 Super-fast WiFi ✅ Sofas+air matress Book now for your unforgettable Chicago stay!
4.89 out of 5 average rating, 19 reviews
Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
Space to live, space to play, space to call home. Our spectacular Two Bedroom Suites boast 1,080 – 1,170 sq ft of modern living space and feature a fully-equipped kitchen, open concept living and dining area, two spa-inspired bathrooms, bedrooms with king beds and an open-air balcony. All suites also feature in-suite laundry, premium appliances, flat-screen TV, complimentary WiFi and local calling.
4.87 out of 5 average rating, 168 reviewsPopular amenities for rentals with a pool near Union Park
House rentals with a pool

1/2 mile to NU, 5min walk to Lake, Swim Spa Pool
5.0 out of 5 average rating, 15 reviews
Luxury fenced in modern ranch
4.83 out of 5 average rating, 6 reviews
Luxury Loft with Private Pool and Movie Theater
4.84 out of 5 average rating, 73 reviews
Rosemont 4BD2BA house with Pool
5.0 out of 5 average rating, 27 reviews
Luxe indoor pool tree house minutes to Chicago
5.0 out of 5 average rating, 3 reviews
Bedford Palace
4.38 out of 5 average rating, 8 reviews
Chic Fulton Market Oasis + Curated Comfort & Style
4.72 out of 5 average rating, 60 reviews
Spacious 2BR in The Loop Downtown Resort Amenities
4.88 out of 5 average rating, 85 reviewsCondo rentals with a pool

Just remodeled apartment close to airport and mall
4.92 out of 5 average rating, 124 reviews
2 bed/2 bath with skyline views
5.0 out of 5 average rating, 9 reviews
Red Door
5.0 out of 5 average rating, 9 reviews
Best view and luxury style, Located in Downtown

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
4.96 out of 5 average rating, 146 reviews
"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
4.96 out of 5 average rating, 122 reviews
"Heart of Evanston" 2br +1Bath-0.6miles to NU
4.93 out of 5 average rating, 147 reviews
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
4.96 out of 5 average rating, 121 reviewsOther vacation rentals with a pool

Riverfront Views - Smart Home - Simple Check In
5.0 out of 5 average rating, 15 reviews
Luxury South Loop Apt
5.0 out of 5 average rating, 9 reviews
South Loop | Rooftop With In & Out Parking | 3
4.8 out of 5 average rating, 95 reviews
Loop 1BR | Steps to Millennium Park & Bean
5.0 out of 5 average rating, 15 reviews
Forest Park Oasis - Dog Friendly - Parks - the "L"
4.97 out of 5 average rating, 33 reviews
Fun 5BR 4.5BA, Pool, Hot Tub, Game Rm, Near O’Hare
5.0 out of 5 average rating, 64 reviews
1bd w/gym, game room, parking. Sleeps 3
4.76 out of 5 average rating, 25 reviews
Long term rental-1 b pool house-no pool parties!
5.0 out of 5 average rating, 17 reviewsQuick stats about rentals with a pool near Union Park

Total vacation rentals
Explore 10 vacation rentals in Union Park

Nightly prices starting at
Union Park vacation rentals start at $320 CAD per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Union Park vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Union Park rentals

4.7 Average rating
Union Park stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
- Garfield Park Conservatory





