Uptown (Chicago), Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Uptown (Chicago), Illinois on RentalSaver.com!

Uptown (Chicago) Rentals

From $1337 per night (USD)
VRBO
Wrigley 4BR Home, Sleeps 10, Firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience Wrigley Ville in this spacious 4-bedroom, 2-bath home, perfect for groups. The house combines two units, offe ...
From $1337 per night (USD)
VRBO
From $484 per night (USD)
Expedia
Wrigleyville 2BR w/Parking, Firepit & Workspace for Remote Work
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the charm of Chicago’s North Side in this cozy 2-bedroom, 1-bathroom apartment, just steps from iconic Wrigley ...
From $484 per night (USD)
Expedia
From $310 per night (USD)
VRBO
2BR Wrigleyville Apt Free Parking, Office, Fire Pit & Outdoor Space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Chicago retreat! This cozy 2-bedroom, 1-bathroom apartment in vibrant Wrigleyville offers everyt ...
From $310 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Four bedroom - 2 bathroom apartment
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Located in the middle of Chicago's Iconic Boystown in the Lakeview neighborhood, this four bedroom (2 queen beds, 2 full ...
From $387 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Stay in the heart of East Lakeview on Halsted!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom condo is in an incredibly convenient Lakeview location for all the life and culture found in Lakeview, wh ...
From $309 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Vibrant 3BR Flamingo Paradise | Heart of Lakeview!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Discover Flamingo Paradise in the BEST location - Lakeview’s Southport Corridor! A stylish 3-bedroom, 2-bath mi ...
From $413 per night (USD)
Expedia
From $191 per night (USD)
VRBO
Bright & Modern Lakeview Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Bring the whole family for a memorable stay in a chic setting. The Space: The bedrooms feature comfortable bed ...
From $191 per night (USD)
VRBO
Click For Pricing
Expedia
Amazing Edgewater 2BR, nr Lake Michigan, by Blueground
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Edgewater Beach furnished two bedroom ...
Click For Pricing
Expedia
From $794 per night (USD)
VRBO
Eddy House, Roscoe Village Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Steps away from Roscoe Village dining & shopping and a short train to the Mag Mile. Enjoy the best Chicago has to offer ...
From $794 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This newly updated 2 bedroom, 1 bath condo has everything you need to make your Chicago stay perfect! The home was thou ...
From $202 per night (USD)
Expedia
From $829 per night (USD)
VRBO
Wrigley 2 bedroom 2 bath with free parking & yard!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: My home is a very large 2 bedroom 2 bath condo 3 blocks (6 minute stroll) from Wrigley Field. It's 20 minutes ...
From $829 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your stay in this 3-BR/2-bath vintage duplex unit located on a serene, residential side street walking distance to ...
From $295 per night (USD)
Expedia
From $155 per night (USD)
VRBO
Cozy Studio In Lakeview, Near Wrigley field
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lakeview is a great location with a mixed residential and business feel. This newly redecorated studio is larger than mo ...
From $155 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Welcoming 2-bedroom apartment with AC in vibrant Chicago Andersonville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Get ready to relax in this cozy and artistic 2 bedroom 1 bath apartment on a quiet tree-lined street in Chicago's Edgewa ...
From $172 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Pristine Lakeview l Boystown l Wrigley Haven l Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the beauty of Chicago from this 1-bedroom apartment in one of the best neighborhoods. This marvelous space offe ...
From $362 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Clean & Equipped 2BR Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Clean, well-furnished 2-bedroom with everything in place. The Space: Our place has a cozy living room, a full ...
From $231 per night (USD)
Expedia
From $954 per night (USD)
VRBO
Lucky Green - A Bold 9BR/5BA w/ Parking by Wrigley
Bedrooms:
5
Bathrooms:
9
Sleeps:
19
This 9BR/5BA space is a 7-minute walk from Wrigley Field and perfect for large groups. 3 living rooms, 3 kitchens, and t ...
From $954 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Beautiful Newly Renovated 3BR/2BA in the Heart of Andersonville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the unparalleled comfort and style of this brand-new, fully renovated 3-bedroom, 2-bathroom condo nestled in ...
From $174 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Wrigleyville Inn - Garden Unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Completely rehabbed 2 bedroom 1 bathroom high end, garden floor condo in a historic greystone, 5 minutes walk to Wrigley ...
From $300 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
La Maison Verte is a Parisian-inspired 2nd floor walk up in a traditional Chicago 2 flat with vintage charm and modern a ...
From $345 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Spacious House ~3min walk WrigleyField~Free Prkg
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience Wrigleyville by staying in this stylish 3BR 2BA gem nestled just 3 mins walk from the famous Wrigley ...
From $481 per night (USD)
VRBO
From $1049 per night (USD)
VRBO
Historic Edgewater Home Steps to the Beach
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
*Reduced new listing price February-March* This 6-bedroom, 3.5 bath home is full of Chicago charm. The house was built ...
From $1049 per night (USD)
VRBO
From $157 per night (USD)
VRBO
Airy Lakeview Studio, w/ W/D, Gym, near Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this studio apartment in Lake View East with high floor views over the city. It’ll be ...
From $157 per night (USD)
VRBO
From $415 per night (USD)
Expedia
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
That's right NO NEIGHBORS ABOVE OR BELOW - It is ALL YOURS! Rare, Private, Freestanding House right in Heart of the city ...
From $415 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...
From $153 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Spacious 4-bedroom condo in wonderful Chicago with WiFi, AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Chicago is waiting for you at this 4-bedroom condo. Step into this enchanting space with 3 queen beds and 1 king bed, pe ...
From $529 per night (USD)
VRBO
From $1102 per night (USD)
VRBO
Wrigleyville 3BD Condo (2)
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1102 per night (USD)
VRBO
From $310 per night (USD)
VRBO
North Chicago Home Su
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 4 bedrooms, and is step ...
From $310 per night (USD)
VRBO
From $476 per night (USD)
VRBO
Wrigleyville 3BR: Game Day Haven with Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Great location in the heart of Wrigleyville! Less than a 5 minute walk from Wrigley Field and a block away from The Metr ...
From $476 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Wrigleyville Getaway
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Summary: Right next to Wrigley Field, and everything the popular Wrigleyville has to offer. ABOVE a very popular Wrigley ...
From $261 per night (USD)
VRBO
From $350 per night (USD)
VRBO
2BR Apartment in Andersonville Neighborhood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 bedroom apartment in a prime location, 2 minutes from the center of Andersonville shopping and dining. Easy access to ...
From $350 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Hip Edgewater 2BR w/ Patio Deck, near Beach & Red Line, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Edgewater Beach. It’ll be easy to simply show up and st ...
From $231 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You won't want to leave this stunning Wrigleyville duplex, located just steps from Chicago's legendary Wrigley Field! T ...
From $159 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Spacious 3BR in Lakeview - Walk to Wrigley - Family Friendly, Newly Renovated!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Chicago and Lakeview! From this apartment, you’re a 10-15 minute walk from Wrigley field, 15-20 minutes from ...
From $360 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Charming 2-bedroom 1 block to Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The whole group will enjoy easy access to everything from this centrally located place, less than a 5-minute walk to the ...
From $381 per night (USD)
VRBO
From $1167 per night (USD)
Expedia
Retro Disco Cowboy Fun, Walk to Wrigley, Restaurants/Bars! 15 mins to downtown!
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Welcome to the ultimate Disco Cowboy getaway! This huge house is perfect for bach parties and friends/family trips! Loc ...
From $1167 per night (USD)
Expedia
From $705 per night (USD)
VRBO
wriglelyville 4BR Retreat New Build + Parking + 1min walk cta
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This brand-new 4-bedroom 3-bath luxury home is located in the heart of Wrigleyville just 1 minute from the Red Line Addi ...
From $705 per night (USD)
VRBO
From $800 per night (USD)
Expedia
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $800 per night (USD)
Expedia
From $1370 per night (USD)
VRBO
Luxurious, custom built single family home near Wrigley
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to one of the best home rentals in Chicago! Built in 2015, this 5 bedroom, 6 bathroom also boasts has an office, ...
From $1370 per night (USD)
VRBO
From $1215 per night (USD)
Expedia
Huge Jungle Retreat w/Ping Pong + Huge Basement. Walk to Wrigley, Restaurants
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Welcome to our jungle-themed retreat in Wrigleyville! *Sleeps 15 guests, has 6 bedrooms & 3 full bathrooms (can sleep u ...
From $1215 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Spacious Wrigley Duplex | Large Entertainment Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our spacious and stylish apartment, located just steps away from the iconic Wrigley Field in Chicago! This is ...
From $563 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Wrigley Field Views & Cubs Vibes – Stay Across the Street!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay Steps from Wrigley Field – Book Your Dream Chicago Getaway Fast!Now Accepting 2025 Cubs Season Bookings! -1 parkin ...
From $455 per night (USD)
Expedia
From $742 per night (USD)
VRBO
LARGE LUX 6BD, 4BA HOME +garage & patio
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Escape into this Chicago Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retail on ...
From $742 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Cozy Train Vibes + Rare Parking x3
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a neighborhood feel in a big city. Welcome to our North Center 3 bedroom, 2 bathroom apartment on a quiet tree lin ...
From $351 per night (USD)
Expedia
From $178 per night (USD)
VRBO
MODERN COMPLETELY REMODELED Bright, Spacious Flat STEPS from Wrigley Field &Bars
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LOCATION! LOCATION! LOCATION!!! You will absolutely love this NEWLY REMODELED 1100 sq ft apartment in the HEART OF WRIG ...
From $178 per night (USD)
VRBO
From $165 per night (USD)
Expedia
A laid-back studio few minutes from Wrigley Field
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your stay in Chicago, Lakeview in this cozy, newly remodeled studio! This studio is located in a walking distance ...
From $165 per night (USD)
Expedia
From $631 per night (USD)
VRBO
Chic 3-Bedroom Condo in Lakeview Central. Private Rooftop, City & Ballpark Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to your stylish Chicago escape! This brand-new, sun-drenched condo blends modern design with unbeatable comfor ...
From $631 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Sunny Andersonville Retreat - 2BD-1BTH + Office
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your urban retreat! This sunny, spacious apartment is situated in the heart of Andersonville. Just half a blo ...
From $317 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Wrigleyville Private Guesthouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New Guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line stat ...
From $447 per night (USD)
VRBO
Click For Pricing
Expedia
Charming House in Lakeview - 1895. Walk to Wrigley
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
About this space Great city living in this bright, comfy, farmhouse style home. Perfect for entertaining with the whole ...
Click For Pricing
Expedia
From $185 per night (USD)
VRBO
Fully restored 1900's 2-Flat on Chicago’s family friendly quiet North Side.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
When I renovated this building my dream was to maintain the look and feel of a 1911 city farmhouse building's charm but ...
From $185 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover Chicago's charm in this newly designed 2-bedroom condo! Located a few blocks away from the heart of Lincoln Sq ...
From $201 per night (USD)
Expedia
From $503 per night (USD)
VRBO
The Wrigleyville Penthouse with Private Rooftop!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Steps from Wrigley Field, my 2 bed/2 bath + Den penthouse with a private rooftop is the perfect “home base” for your gro ...
From $503 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant ...
From $202 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Stylish Two Bedroom - A block from Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come stay at this gorgeous, clean, renovated apartment in beautiful Lakeview/Wrigleyville. The unit is located on a beau ...
From $294 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
If you love Mid-Century Modern decor you will love this apartment. The light- filled main family room and sun porch is ...
From $303 per night (USD)
Expedia
From $964 per night (USD)
VRBO
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to The Wrigleyville Deluxe. Perfect for large groups. 2 full Kitchens. 3 full baths. Sleeps 10. 1 King bed. 4 ...
From $964 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Lovely 3 Bedroom condo near Wrigley!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
My charming 3-bedroom apartment has everything you need for your Chicago trip. The unit comes with washer/dryer in build ...
From $510 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Trendy Lakeview 1BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with views over the city. It’ll be easy ...
From $141 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Large and quiet 1 bedroom 1 bathroom Garden unit located in a typical Chicago 2 flat building type. We are exactly betw ...
From $231 per night (USD)
VRBO
From $287 per night (USD)
VRBO
Warm|Cozy|Lovely|1BR|Lincoln Sq.|
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $287 per night (USD)
VRBO
From $141 per night (USD)
Expedia
Ideal Lakeview 1BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $141 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Comfy Garden Suite in Andersonville
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A comfortable garden unit in a well cared for 3-flat, in a wonderful and safe neighborhood. Easy access to the lake fro ...
From $175 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Cute, Cozy, Elegant Budlong Woods
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Book with us and enjoy classic charm and elegant décor located in the Budlong woods neighborhood. Experience a great nig ...
From $132 per night (USD)
Expedia
From $78 per night (USD)
VRBO
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $78 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Cute and Cozy 2 Bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Enjoy Classic decor in a spacious two bedroom one bathroom. Large eat-in kitchen and laundry in the basement! Tony's gro ...
From $162 per night (USD)
Expedia
From $1021 per night (USD)
VRBO
Luxury Wrigleyville condo steps from Wrigley
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
New construction property that has 4 bedrooms, one with king, two with queen beds, and one with a queen bed and bunk bed ...
From $1021 per night (USD)
VRBO
From $77 per night (USD)
Expedia
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $77 per night (USD)
Expedia

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Uptown (Chicago) Rentals

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Results: 168 Rentals