Uptown Rentals By Owner

There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Uptown:

• Spacious 2-BR Condo + Free On-Site Parking
• ❤️ Spacious and Airy Apartment With Parking On Site!
• Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
• -Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
• Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
• Sunny Modern Loft Montrose Beach Rooftop WFH Gym
• Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered apts
• Designer 3BR with Balcony & Elevator on Clark! apts
• Beautiful Uptown 1BR w/Gym, Rooftop Pool, 2 blocks to L, by Blueground
• Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-383

There are many large, family-friendly vacation homes available in Uptown; however, here are the most popular family rentals listed on our site:

• Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
• Uptown Gem
• Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
• Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway condo

Yes, there are 79 self-catering vacation homes in Uptown that have hot tubs, swimming pools, & other amenities.

There are more than 79 luxury villas and vacation homes in or near Uptown. Filter by price to compare find the most expensive places to stay on Peak8breckenridge.

Yes, there are 79 pet friendly vacation homes and places to stays that are available in or near Uptown that you may consider.