Vacation rentals with a pool in Chicago River

2BR Downtown Elmhurst | Pool, Gym, Kings, Garage

A professionally managed 2-bed 2-bath apartment in downtown Elmhurst, providing the perfect balance of luxury and comfort for business travelers and families. Walk to the cafes, restaurants, and shops of downtown Elmhurst, nearby classy Oakbrook (8 mins), O'Hare airport (12 mins), and blocks to the Metra train station with easy access to downtown Chicago! Enjoy the pool, fitness center, garage parking, courtyard with firepits, pool table, and movie theater - convenience is at your fingertips!

Best view and luxury style, Located in Downtown

Experience the best view of your life Chicago's iconic landmarks from this high-rise apartment. Located downtown,you can see Wacker Drive, the lake, Navy Pier, the river,Trump tower from your balcony and room , The place features a spacious bedroom with a king bed , comes fully equipped with essentials, kitchen. large TV, and high WiFi. With premium amenities pool, spa, hot tub, library ,work area,computers,gym, bar. offers the perfect blend of luxury, comfort for a best city life experience

Long term rental-1 b pool house-no pool parties!

This memorable place is anything but ordinary. Completely rehabbed one bedroom pool house with queen size bed and custom built in sofa that can comfortably sleep an additional two people. Access to private kitchen, pool, outdoor grill and fire pit. Private parking included. Has refrigerator, microwave and coffee maker in kitchen in nearby garage that's completely stocked! Comfortably sleeps 4. Includes pool toys and beautiful landscaping and basketball court. 25 minutes to downtown Chicago.

Forest Park Oasis - Dog Friendly - Parks - the "L"

This newly remodeled two-bedroom home in Forest Park offers comfort and convenience, sleeping four with TVs in every room and a fully equipped kitchen. dog friendly, a dedicated workspace, hardwood floors throughout. Enjoy a formal dining room and electric fireplace. Located across from the park, pool, tennis courts, and Roos Recreation Center, it's just a 5-minute walk to the Harlem Blue Line Station, making downtown Chicago and airports easily accessible. Perfect for both work and leisure!

Music Hotspot 2nd Floor

Urban-style suite with Fiber Wi-Fi walking distance of 4 music venues. Crawling distance from Fitzgerald's music venues. 2 blocks from Autre Monde and other restarnats/stores. 3 blocks to the CTA Blue line & 6 blks CTA Green/Pink line. Close to parks, pools, the zoo, and Thatcher woods/river. Many amenities, including a unique landscape, a fire pit, a furnished patio, kool artwork, smoker, grills, two furnaces and more. Must be 25 years or older to book. Only get togethers - no parties!

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

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. Joy of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

Pond View, Washer Dryer, Non Smoking, Pet Free

Welcome to our cozy retreat! Fully furnished for affordability and convenience, our prime location near Downers Grove, Wheaton, Oakbrook, and Downtown Chicago ensures the perfect base for your stay. Enjoy free parking, washer-dryer, dishwasher, and amenities like linens, dishes, cookware, cable, wireless internet, queen-size bed, smart TV, and Hulu access. Little touches make guests feel truly at home, creating a delightful and memorable stay, whether for business or leisure.

Bedford Palace

Spacious and bright 3-bedroom split - level house, perfect for families or working professionals. Great place to work, relax or spend time with family and friends! Des Plaines offers a mix of entertainment, outdoor recreation, and history, featuring the Rivers Casino, the restored Des Plaines Theatre, and family-friendly spots like Mystic Waters Water Park and Lake Opeka. You can also explore local parks, hike the Des Plaines River Trail, or dine in the vibrant downtown area.

Luxury fenced in modern ranch

Escape to the stunning remodeled, exquisite upscale mid-century modern luxury ranch near downtown Skokie three blocks from the subway, Skokie waterpark and Evanston golf club-and by staying at the stunning property, you are in the heart of Skokie at the edge of downtown with easy access to almost everything! Relax and unwind in my fenced in yard or perhaps use the pizza maker to help make a pizza with the kids! For worship needs, I am 2 blocks away from Church and Temple.

Plains/Chicago Midcentury Guest House

Under new, professional management. Sitting on a midcentury, 1.35 acre private estate close to everything -- O'Hare, Rosemont, Chicago, and much more -- you’ll have exclusive, private use of a detached two bedroom guesthouse and shared access to the sprawling, landscaped backyard featuring a seasonal pool, loungers, and grill. Amenity highlights include: large bedrooms, fully equipped kitchen, smart TVs, central air, WiFi, washer/dryer, and more.

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Modern-Luxe experience at the Unity of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 3 bedrooms, 2 full baths, 1 roll-out bed welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown. This unit is all about bring a family together in UNITY!

Quiet Luxury• Skyline Views• 15 Min to Chicago

Unwind after a long day in the full-body massage chair, take in the beautiful skyline views, or simply enjoy the calm atmosphere—perfect for couples, solo travelers, or professionals needing a reset. Step right across the street to shopping centers, dining, and everyday essentials, so everything you need is within walking distance. Whether you’re here to explore the city or just relax and recharge, this stay makes it easy.