Uptown (Chicago) Rentals
From $128 per night (USD)VRBO
Dreamy Uptown 1BR w/ Gym, Rooftop Pool, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Uptown. It’ll be easy to simply show up and start livin ...
From $128 per night (USD)VRBO
From $237 per night (USD)Expedia
W2 - ❤️ New and Clean! Big Apartment with Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
<p>Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in Uptown neighborhood, near to food, sup ...
From $237 per night (USD)Expedia
From $190 per night (USD)VRBO
The Bright Retreat in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark St ...
From $190 per night (USD)VRBO
From $221 per night (USD)VRBO
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $221 per night (USD)VRBO
From $423 per night (USD)VRBO
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Live like a local in one of Chicago’s best neighborhoods! Located in a family-owned boutique building in the vibrant and ...
From $423 per night (USD)VRBO
From $238 per night (USD)Expedia
Great Location-Beautiful Friendly Andersonville Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
City of Chicago Vacation LICENSE NO.: 2209341 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful t ...
From $238 per night (USD)Expedia
From $435 per night (USD)VRBO
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local in one of Chicago’s best neighborhoods at a top rated property! Located in a family-owned boutique bui ...
From $435 per night (USD)VRBO
From $205 per night (USD)Expedia
Inviting Stylish Home with Covered Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
There are about 5 steps that you have to go down to get to the apartment. Older building with radiant heat managed by th ...
From $205 per night (USD)Expedia
From $201 per night (USD)VRBO
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in the heart of Chicago's premier entertainment district • Walk Score 93 (“Walker’s Paradise”) • Free street par ...
From $201 per night (USD)VRBO
From $458 per night (USD)Expedia
W3 - Spacious 2BR Apt + Free On-site Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $458 per night (USD)Expedia
From $511 per night (USD)VRBO
PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its ...
From $511 per night (USD)VRBO
From $365 per night (USD)VRBO
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bright top-floor Chicago condo with fast WiFi, dedicated workspace, and easy access to Montrose Beach and the CTA. Perf ...
From $365 per night (USD)VRBO
From $133 per night (USD)VRBO
Beautiful Uptown 1BR w/ Gym, Rooftop Pool, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $133 per night (USD)VRBO
From $511 per night (USD)VRBO
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its ...
From $511 per night (USD)VRBO
From $1033 per night (USD)VRBO
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1033 per night (USD)VRBO
From $326 per night (USD)Expedia
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲 ...
From $326 per night (USD)Expedia
From $179 per night (USD)VRBO
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲 ...
From $179 per night (USD)VRBO
From $268 per night (USD)Expedia
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲 ...
From $268 per night (USD)Expedia
From $730 per night (USD)VRBO
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Your cozy getaway awaits in Chicago at this superb apartment. With 4 bedrooms including 1 king, 1 queen, and 2 full beds ...
From $730 per night (USD)VRBO
From $229 per night (USD)Expedia
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲 ...
From $229 per night (USD)Expedia
From $881 per night (USD)VRBO
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.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, ...
From $881 per night (USD)VRBO
From $549 per night (USD)Expedia
Chic Vintage Stay w/ Private Balcony – Walk to Argyle Redline, Lake, Dining
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Step into vintage charm at Maison Winona, a 1908 Prairie School stunner by Chicago architect Frederick Schock, in the he ...
From $549 per night (USD)Expedia
From $1329 per night (USD)VRBO
Massive Queen Anne Mansion for your whole family to stay!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
This is your chance to stay in a historic Chicago mansion. This beautiful Queen Anne style mansion has an abundance of c ...
From $1329 per night (USD)VRBO
From $661 per night (USD)Expedia
Stay at The Velvet Manor, a beautifully designed 3BR home just steps from Andersonville's vibrant Clark Street. Enjoy spacious living, a chef's kitchen, dedicated office, Jacuzzi tub, outdoor area, and garage parking.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Velvet Manor, a moody, designer-curated 3-bedroom retreat in the heart of Andersonville. Unwind in richly ...
From $661 per night (USD)Expedia
From $488 per night (USD)VRBO
The Velvet Manor | 2BR Boutique Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Velvet Manor, a moody, designer-curated 2-bedroom retreat in the heart of Andersonville. Unwind in richly ...
From $488 per night (USD)VRBO
From $164 per night (USD)Expedia
2BR/2BA · pet-friendly · workspace · residential garage parking · king beds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bed/2 bath with stainless steel appliances, king beds, standing desk, fenced backyard, dog beds/bowls, and shared laun ...
From $164 per night (USD)Expedia
From $667 per night (USD)VRBO
Spacious Chicago Group Home! Walk to Train & Eats
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Game Room + Yard | 7 Mi to Downtown | Bring Your Pets This 3-bed Chicago vacation rental is perfect for families and gr ...
From $667 per night (USD)VRBO
From $307 per night (USD)Expedia
Walk to Wrigley! Spacious 3BR in the Heart of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
1 mile to Wrigley! Bright and inviting 3-bedroom, 1-bath apartment in Chicago’s Edgewater neighborhood—sleeps up to 7 gu ...
From $307 per night (USD)Expedia
From $296 per night (USD)VRBO
Chicago Gem: Wrigley - Lakefront - Red Line Train
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of city excitement and neighborhood charm in this spacious 2-bedroom, 1-bath condo located in ...
From $296 per night (USD)VRBO
From $217 per night (USD)VRBO
Pet-Friendly Uptown Chicago Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
Summary: 2 bedroom Unit in Uptown Chicago The Space: 2 bedroom home with 2 bathrooms that sleeps 11. Bed sizes a ...
From $217 per night (USD)VRBO
From $232 per night (USD)VRBO
Vibrant, walkable Andersonville Gem-easy access to Wrigley, venues and Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. With 3 comfortable bedrooms featuring 2 queen beds and 1 king bed, gues ...
From $232 per night (USD)VRBO
From $230 per night (USD)Expedia
The Shingle Life near Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: I took a perfectly nice little flat on a beautiful street and filled it with great things...I want my guests t ...
From $230 per night (USD)Expedia
From $217 per night (USD)VRBO
A Hand-some Place Near Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: I’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a sus ...
From $217 per night (USD)VRBO
From $115 per night (USD)VRBO
Detached, private, spacious, free garage, fast wifi, 5min to metra in Ravenswood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Fully renovated in July 2025, this charming detached coach house from 1897 blends historic character with modern comfort ...
From $115 per night (USD)VRBO
From $260 per night (USD)VRBO
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away on a quiet, tree-lined street in Chicago’s Uptown / Sheridan Park, this beautifully renovated 2-bedroom, 1-b ...
From $260 per night (USD)VRBO