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 $1116 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 $1116 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Andersonville Charming 3 Bedroom/2 Bath House with Family Room plus Yard & Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED sing ...
From $279 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Elegant 2BR Apartment w/ In-Unit Laundry
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to your stylish Uptown escape! This bright 2BR/2BA is perfect for families, friends, or work trips. Wit ...
From $293 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Delightful 1BR Apt in Ravenswood
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Discover a one-of-a-kind escape in this uniquely styled 1-bedroom apartment. With modern design, cozy furnishin ...
From $231 per night (USD)
Expedia
From $978 per night (USD)
VRBO
Ultra Modern Luxury - New Construction 4 Bedrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
New Listing! New Construction! Ultra modern 2500 SF+ Four Bedroom Duplex Condo in the heart of Chicago’s Uptown/ Edgewa ...
From $978 per night (USD)
VRBO
From $95 per night (USD)
Expedia
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 $95 per night (USD)
Expedia
From $336 per night (USD)
VRBO
❤️ Spacious and Airy Apartment With Parking On Site!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $336 per night (USD)
VRBO
From $222 per night (USD)
Expedia
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 $222 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
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 $227 per night (USD)
VRBO
From $764 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 $764 per night (USD)
VRBO
From $216 per night (USD)
VRBO
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 $216 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Inviting Stylish Home with Covered Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan mai ...
From $408 per night (USD)
Expedia
From $616 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 $616 per night (USD)
VRBO
From $412 per night (USD)
Expedia
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 $412 per night (USD)
Expedia
From $1481 per night (USD)
VRBO
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Bedrooms:
3
Bathrooms:
6
Sleeps:
21
Time Out magazine calls us one of the Best Chicago Rentals! HUGE mansion with six bedrooms, two living rooms, and four ...
From $1481 per night (USD)
VRBO
From $287 per night (USD)
VRBO
Spacious 2-BR Condo + 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 $287 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $229 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Elegant Hideaway in the Heart of Andersonville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This beautifully designed hideaway is just a block away from the heart of Andersonville. The spacious interior provides ...
From $303 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Sunny Studio in Heart of Ravenswood
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Stay at this bright and cozy studio on N Ashland Ave! Walk to iconic spots like the Green Mill, Montrose Beach, ...
From $188 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Uptown Studio Gem Sum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy the best of Chicago’s North Side from this bright and comfortable studio apartment located on W Montrose ...
From $194 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Chic Vintage Stay w/ Private Balcony – Walk to Argyle Redline, Lake, Dining
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step into vintage charm at Maison Winona, a 1908 Prairie School stunner by Chicago architect Frederick Schock, in the he ...
From $609 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Majestic Modern Style|13 mins DT|4 mins Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $240 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Chic apartment in marvelous Chicago with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Escape to our Eclectic Boho Chic Suite, where vibrant style meets modern comfort. With breathtaking views of Montrose Ha ...
From $229 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Your cozy getaway awaits in Chicago at this superb apartment. With 4 bedrooms including 1 king, 1 queen, and 2 full beds ...
From $503 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $172 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Montrose Studio:Your Uptown Base
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Summary: Discover the perfect blend of city excitement and neighborhood tranquility in our charming studio apartment loc ...
From $194 per night (USD)
Expedia
From $369 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 - it ...
From $369 per night (USD)
VRBO
From $123 per night (USD)
Expedia
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 $123 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy Studio in Bustling Ravenswood Neighborhood
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This small but cozy apartment is located in the heart of Ravenswood near amazing restaurants and bars, close to Wrigley ...
Click For Pricing
VRBO
From $1073 per night (USD)
Expedia
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Our home is located in the quiet, but centrally located Buena Park neighborhood in an updated antique building. The loca ...
From $1073 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $214 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $196 per night (USD)
Expedia
Click For Pricing
VRBO
Chicago Home w/ Hot Tub < 2 Mi to Wrigley Field
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
- R23000095595 - 3,000 Sq Ft - Projector - Spacious Backyard - 8 Mi to Downtown Chicago Explore the vibrant city of Chi ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Chic studio apartment in central location in Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to this enchanting apartment in Chicago. This cozy space features a studio with a comfortable twin bed, perfect ...
Click For Pricing
Expedia
From $272 per night (USD)
VRBO
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and conve ...
From $272 per night (USD)
VRBO
From $210 per night (USD)
VRBO
Homey|Vintage|2BR Uptown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming & Vintage 2 bedroom, 1 bath with plenty of living space. Conveniently located in the middle of several vibrant ...
From $210 per night (USD)
VRBO
From $384 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 - it ...
From $384 per night (USD)
VRBO
From $1091 per night (USD)
Expedia
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up and ...
From $1091 per night (USD)
Expedia
From $1097 per night (USD)
VRBO
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Located inside one of the iconic Wrigley Rooftops, and just a few steps away from Wrigley Field, this apartment offers a ...
From $1097 per night (USD)
VRBO
From $1097 per night (USD)
Expedia
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to the Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up ...
From $1097 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Experience city life; Located in Wrigley! Feel like a local! We're experienced! we've hosted more than 1000 reservati ...
From $336 per night (USD)
VRBO
From $1278 per night (USD)
Expedia
New home w/view & party deck - 2nd Floor
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1278 per night (USD)
Expedia
From $1166 per night (USD)
VRBO
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1166 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Wonderful Edgewater 1BR w/ Patio Deck & Gym, near lake, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. It’ll be easy to simply show up and st ...
From $157 per night (USD)
Expedia
From $343 per night (USD)
VRBO
2-bedroom apartment just 2 minutes drive to Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $343 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Lakeview Lux - Apt #2
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $140 per night (USD)
Expedia
From $153 per night (USD)
VRBO
Lakeview Lux - Apt #1
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $153 per night (USD)
VRBO
From $585 per night (USD)
Expedia
St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...
From $585 per night (USD)
Expedia
From $224 per night (USD)
VRBO
2BR Steps from Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to your home base in the heart of Chicago’s vibrant Lakeview/Wrigleyville neighborhood! This roomy and ...
From $224 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Stylish 1BR in Lakeview Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Step into comfort and style in this beautifully designed 1-bedroom apartment nestled in vibrant Lakeview. With ...
From $246 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Cozy & Modern Getaway 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A chic spot to kick back, relax, and enjoy some fun together. The Space: This charming home has plenty of spac ...
From $236 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Vibrant 1BRApt in Roscoe Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The perfect blend of comfort and style for a fun, relaxing stay. The Space: This charming home has plenty of s ...
From $241 per night (USD)
Expedia
From $246 per night (USD)
VRBO
1BR Modern Apt near City center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This unique place has a style all its own. The Space: This charming home has plenty of space for everyone to r ...
From $246 per night (USD)
VRBO
From $254 per night (USD)
Expedia
1BR Chic & Sunny Place
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Feel at home in our furnished 1-bedroom with a comfy living room, full kitchen, and private bath. Everything yo ...
From $254 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Cozy 3BR Gem in North Center
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: This spacious and stylish 3-bedroom gem is perfect for families, groups, or business travelers seeking comfort ...
From $537 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Boystown Chic 2BR Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Unwind in this stylish 2BR retreat, where cozy comfort meets modern charm. Thoughtfully designed with chic déco ...
From $244 per night (USD)
Expedia
From $306 per night (USD)
VRBO
1BR Pad with Homey Feel
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Our place includes a bedroom, comfy living room, kitchen, and bathroom, plus some extra touches for added comfo ...
From $306 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Stylish and Roomy 2BR in Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Enjoy plenty of space to relax in this cozy, well-appointed home featuring comfy bedrooms, a fully stocked kitc ...
From $261 per night (USD)
Expedia
From $228 per night (USD)
VRBO
1BR/1BA City Comfort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Our one-bedroom apartment offers a perfect balance of style, simplicity, and ease, ideal for travelers looking ...
From $228 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Cozy & Furnished 2BR Unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Fully furnished 2-bedroom with all the comforts you need for a great stay. The Space: A fully furnished 2-bedr ...
From $217 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Comfy 2BR in Heart of Lakeview
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to your Lakeview escape! This bright and cozy 2-bedroom apartment is perfectly located on W Grace St, j ...
From $321 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Nice 1BR Spot, Unwind & Relax
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Simple, cozy space to relax. Fully furnished and ready for your stay. The Space: Enjoy a comfy and convenient ...
From $235 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Modern 2BR with Reliable Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This stylish and spacious 2-bedroom unit is ideal for families, friends, or business travelers. Featuring a ful ...
From $333 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Bright 1BR Classic Chicago Feel
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Kick back and stay a while in this 1-bedroom apartment that brings old-school Chicago charm with just the right ...
From $232 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Cozy 1BR in Walkable Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to a cozy 1BR in the heart of Chicago’s Ravenswood/Lincoln Square neighborhood. Located on a quiet, tre ...
From $231 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Feel at Home in our 2BR Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our place! It’s a cozy and laid-back 2-bedroom apartment that’s perfect for relaxing after a day out ...
From $325 per night (USD)
Expedia
From $181 per night (USD)
VRBO
1BR Apartment in Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A clean and well-appointed space, easy place to settle in. The Space: My fully furnished 1-bedroom apartment h ...
From $181 per night (USD)
VRBO
From $254 per night (USD)
Expedia
1BR Well-Equipped Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: All the comforts of home in a stylish, fully furnished 1BR—ideal for short or long stays. The Space: Our fully ...
From $254 per night (USD)
Expedia
From $191 per night (USD)
VRBO
1BR Cozy Apt with King-sized Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Step into a space that’s truly one of a kind—this unique 1-bedroom apartment has a style all its own. Thoughtfu ...
From $191 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Clean & Equipped 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Our 1-bedroom apartment is fully furnished and perfect for anyone who just wants to settle in and feel at home. ...
From $244 per night (USD)
Expedia
From $244 per night (USD)
VRBO
2BR Apt Beautifully Furnished - Grace 11-1
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Come unwind in our warm and inviting 2-bedroom apartment. It’s beautifully furnished with comfy beds, a fully e ...
From $244 per night (USD)
VRBO
From $311 per night (USD)
Expedia
2BR on N Halsted St: Lakeview Living
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Immerse yourself in the vibrant energy of Chicago's North Side from our lovely 2-bedroom apartment on N Halsted ...
From $311 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Homey 1BR Space Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: A modern and fully furnished 1-bedroom apartment designed with stylish, carefully curated touches that create a ...
From $231 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Relaxing Lakeview Escape 2BR Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Experience comfort and calm in this lakeview 2-bedroom apartment, ideal for families, friends, or professionals ...
From $339 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Prime Location! 2BR Near Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Make yourself at home in this bright and inviting 2-bedroom apartment, nestled in the lively and sought-after W ...
From $320 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Modern & Well-Located 1BR Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy a stylish stay in this freshly designed 1-bedroom apartment, where modern finishes meet cozy comfort. Tho ...
From $289 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Cute 1BR in Heart of Lincoln Sq
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Cute apartment near Lincoln Square shops and restaurants. Lively area near public transportation. Near the lake ...
From $247 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Deluxe 1BR Near Shops & Cafés
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Enjoy the perfect blend of comfort and location in this stylish 1-bedroom apartment. Featuring a cozy living sp ...
From $263 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Cozy studio in Andersonville Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This newly constructed studio offers a stylish, modern space just steps from Clark Street—home to some of the best resta ...
From $172 per night (USD)
VRBO
From $208 per night (USD)
Expedia
Luxurious 3 Bedroom Apartment in Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Your cozy getaway awaits in Chicago at this fabulous house. With 3 bedrooms including 2 queen beds and 1 sofa bed, this ...
From $208 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Serene 3-bedroom apartment in Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to our stunning retreat, perfect for families or friends seeking a stylish getaway. This beautifully designed un ...
From $275 per night (USD)
VRBO
From $195 per night (USD)
Expedia
New Listing /20% Discount 32+/ Fast Wi-Fi / 1 Parking Spot!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Highly sought-after North Center / St. Ben's Location -1 Garage Spot INCLUDED!! - Fully furnished unit with everything ...
From $195 per night (USD)
Expedia
From $456 per night (USD)
VRBO
Andersonville Charming 3 Bedroom/2 Bath House with Family Room plus Yard & Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED singl ...
From $456 per night (USD)
VRBO
From $1184 per night (USD)
Expedia
2-Story 4-Bedroom Condo: 3-minute walk to Wrigley Field. King Bed
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Just one block from Wrigley Field! Includes air hockey, ping-pong, foosball, and oversized Connect 4 in the basement ga ...
From $1184 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers every ...
From $322 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Wrigleyville Suites Room 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $185 per night (USD)
Expedia
From $325 per night (USD)
VRBO
The Burrow at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Expect to find a relatively dark and moody interior filled with interesting things. The location is exceptional, with th ...
From $325 per night (USD)
VRBO
From $1275 per night (USD)
Expedia
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Bedrooms:
5
Bathrooms:
10
Sleeps:
26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1275 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This central location can't be beat! Situated on the border of Lakeview and Wrigleyville and only 1 mile from historic ...
From $234 per night (USD)
VRBO
From $2668 per night (USD)
VRBO
Vacation home just 2 minutes drive to Wrigley Field
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, ...
From $2668 per night (USD)
VRBO
From $537 per night (USD)
VRBO
NEW! Charming 3bd Bungalow in Vibrant Andersonville by AllSet Turnover
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to our vintage Andersonville bungalow! Built in the 1920s, our home exudes character with original floors, wind ...
From $537 per night (USD)
VRBO
From $700 per night (USD)
VRBO
Gracious, spacious vintage home in a terrific neighborhood near the lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A house with real character and color. Filled with art, much by the artist who lives in it. Lots of warm oak floors and ...
From $700 per night (USD)
VRBO
From $1242 per night (USD)
VRBO
Wrigleyville 3BD Condo
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 $1242 per night (USD)
VRBO
From $1131 per night (USD)
VRBO
Wrigleyville Garden 3BR/9beds Pod
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1131 per night (USD)
VRBO
From $611 per night (USD)
VRBO
Updated 3 Bedroom Chicago Historic Andersonville
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $611 per night (USD)
VRBO
From $2448 per night (USD)
VRBO
Six-Bedrooms in Wrigleyville
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...
From $2448 per night (USD)
VRBO
From $580 per night (USD)
VRBO
Game Day Getaway - 3BR in Vibrant Wrigleyville
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
An excellent location in the vibrant heart of Wrigleyville! It's a brief 5-minute stroll to Wrigley Field and just aroun ...
From $580 per night (USD)
VRBO
From $1269 per night (USD)
VRBO
Modern 6BR House Steps to Wrigleyville
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Fantastic location in the heart of Wrigleyville! Just a 5-minute walk to Wrigley Field and a block from The Metro concer ...
From $1269 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Mid-Century Modern 2 BD APT | Walk to Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience stylish comfort in this beautifully designed, mid-century modern apartment in the heart of Wrigleyville. Enjo ...
From $352 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Blissful Chicago Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a beautiful apartment only a short walk away from Clark street which features amazing nightlife and some of the ...
From $230 per night (USD)
VRBO

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Results: 258 Rentals