Uptown (Chicago) Rentals
- From $500 per night (USD)
VRBO
-Lovely 5 BedRoom Unit in Uptown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $500 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Uptown furnished one bedroom ap ...
From $147 per night (USD)VRBO
- Click For Pricing
VRBO
Barsala l Spacious, bright 1BD w\/ Fitness Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Situated in Uptown Chicago, our modern and bright apartments are minutes away from countless options for dining and meet ...
Click For PricingVRBO
- From $113 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 liv ...
From $113 per night (USD)VRBO
- From $333 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 $333 per night (USD)VRBO
- From $231 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 $231 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $537 per night (USD)
VRBO
3 Bedroom\/ 2 Bathroom Luxury Condo 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 $537 per night (USD)VRBO
- From $167 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 $167 per night (USD)VRBO
- From $478 per night (USD)
VRBO
2BD\/2BA Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel
- 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 $478 per night (USD)VRBO
- From $291 per night (USD)
VRBO
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 $291 per night (USD)VRBO
- From $319 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 $319 per night (USD)VRBO
- From $172 per night (USD)
VRBO
2BR in Andersonville-Walk to train, beach, shops and restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom apartment right in Historic Uptown / Andersonville. One block from CTA redline and one block from Clark Stre ...
From $172 per night (USD)VRBO
- From $1150 per night (USD)
VRBO
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
- Bedrooms:
- 4
- 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 $1150 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Uptown 1BR w\/ Roof & W\/D, 1 block to Red Line, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Uptown. with views over the city. It’ll be easy to simp ...
Click For PricingVRBO
- Click For Pricing
VRBO
Bright Uptown 1BR w\/ W\/D & Roof, near Aragon Ballroom, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Uptown furnished one bedroom apartm ...
Click For PricingVRBO
- From $438 per night (USD)
VRBO
❤️ Lowest Rates! Spacious Duplex with Free Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $438 per night (USD)VRBO
- From $128 per night (USD)
VRBO
Airy Uptown 1BR w\/ Fire Pits & Indoor Pool, nr Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $128 per night (USD)VRBO
- From $89 per night (USD)
VRBO
Hip Uptown 1BR w\/ Rooftop & Grills, nr Hospital & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Uptown furnished one bedroom apartment w ...
From $89 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Charming Uptown 1BR w\/ Indoor Pool, nr Lakefront Trail, 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 $150 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Bright Uptown 1BR w\/ Gym w\/ Boxing Ring, nr Red Line, 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 $165 per night (USD)VRBO
- From $75 per night (USD)
VRBO
Amazing Uptown 1BR w\/ Gym & Indoor Pool, nr L Red Line, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Uptown furnished one bedroom apartment ...
From $75 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Free Parking Luxury Loft Getaway Uptown Montrose Beach WFH Gym Pet Friendly
- 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 $147 per night (USD)VRBO
- From $164 per night (USD)
VRBO
Majestic Modern Style Loft Montrose Beach WFH Gym RARE. Pet Friendly
- 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 $164 per night (USD)VRBO
- Click For Pricing
VRBO
Barsala l Modern studio, fitness center & kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Situated in Uptown Chicago, our modern and bright apartments are minutes away from countless options for dining and meet ...
Click For PricingVRBO
- From $195 per night (USD)
VRBO
Full of Charm Studio Apartment Nearby Shops
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Experience a serene getaway in our charming studio apartment designed with your comfort and relaxation in mind. Our plus ...
From $195 per night (USD)VRBO
- From $271 per night (USD)
VRBO
Luxe 2BR Apartment w\/ In-Unit Laundry
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our luxurious 2 bedroom apartment! Our home includes fully furnished kitchen, modern bathroom, in-unit laundr ...
From $271 per night (USD)VRBO
- Click For Pricing
VRBO
PRIVATE Boho vintage condo with sunrooms and plants in Historic Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Overview: You'll be set up with a traditional 3rd-floor walk-up, Chicago railroad-style living space, and beautiful orig ...
Click For PricingVRBO
- From $810 per night (USD)
VRBO
Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
There's room for 12 between my 2 apartments (one just above the other) in Sheridan Park, and it's a stunning place to ca ...
From $810 per night (USD)VRBO
- From $524 per night (USD)
VRBO
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by RedAwning
- 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 $524 per night (USD)VRBO
- From $127 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 $127 per night (USD)VRBO
- Click For Pricing
VRBO
Dreamy Uptown Studio w\/ Roof & W\/D, near Aragon Ballroom, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Uptown. with views over the city. It’ll be easy to simply sh ...
Click For PricingVRBO
- From $183 per night (USD)
VRBO
1BR Delightful Apt in Ravenswood | Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious 1-bedroom, 1 bathroom apartment is remodeled for you to enjoy. The unit comes with granite countertops, st ...
From $183 per night (USD)VRBO
- From $161 per night (USD)
VRBO
Elite Studio Apartment in Uptown near Shops
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Experience the ultimate urban retreat in this stylish and sophisticated studio located in the vibrant Uptown neighborhoo ...
From $161 per night (USD)VRBO
- From $314 per night (USD)
VRBO
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 $314 per night (USD)VRBO
- From $181 per night (USD)
VRBO
Cozy Uptown Studio with In-unit laundry & Wi-Fi!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Welcome to our exquisite fully furnished studio unit in the heart of Uptown Chicago. Experience the ultimate urban retre ...
From $181 per night (USD)VRBO
- From $177 per night (USD)
VRBO
Studio Apartment w\/ In-Unit Laundry, Near Shops!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Welcome to our fully-furnished studio with a bright living space, equipped kitchen, modern bathroom, and in-unit laundry ...
From $177 per night (USD)VRBO
- From $106 per night (USD)
VRBO
Hidden Andersonville \/ Wrigleyville Gem!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Relax with friends and family at this hidden Andersonville / Gem. This peaceful and spacious unit is located in the hear ...
From $106 per night (USD)VRBO
- 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 PricingVRBO
- Click For Pricing
VRBO
Large 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is located in the quiet, but centrally located Buena Park neighborhood in an updated antique building. The loca ...
Click For PricingVRBO
- From $437 per night (USD)
VRBO
Eclectic Home w\/ Hot Tub < 2 Mi to Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Explore the vibrant city of Chicago, IL, when you book this spacious 4-bedroom, 2.5-bathroom vacation rental. Staying in ...
From $437 per night (USD)VRBO
- From $138 per night (USD)
VRBO
Artistic Stylish Modern Loft Uptown Getaway RARE\n\n
- 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 $138 per night (USD)VRBO
- From $148 per night (USD)
VRBO
Maisons de Promettre\nModern Elegance Suite in the Heart of Uptown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Chicago stands as an architectural marvel and bastion of cosmopolitan prestige. Elevate your trip with timeless elegance ...
From $148 per night (USD)VRBO
- From $182 per night (USD)
VRBO
Regal Stylish Loft Uptown Montrose Beach - Serene Getaway WFH Gym Pets Allowed\n\n
- 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 $182 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Luxury Modern Uptown Studio Loft Serene Montrose Beach WFH Gym Pet Friendly\n\n
- 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 $147 per night (USD)VRBO
- From $139 per night (USD)
VRBO
Elegant Modern Stylish Loft Mountain Vibe Montrose Beach WFH Gym Pet Friendly\n\n
- 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 $139 per night (USD)VRBO
- From $93 per night (USD)
VRBO
Deluxe Uptown 1BR w\/ Gym, Pool & Rooftop, nr Red Line, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Uptown furnished one bedroom ap ...
From $93 per night (USD)VRBO
- From $115 per night (USD)
VRBO
Chic Uptown 1BR w\/ Rooftop & Gym, nr Hospital & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Uptown furnished one bedroom apartment ...
From $115 per night (USD)VRBO
- From $161 per night (USD)
VRBO
Delightful Uptown 1BR w\/ Indoor Pool, 2 Blocks to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Uptown. with views over the city. It’ll be easy to simp ...
From $161 per night (USD)VRBO
- From $113 per night (USD)
VRBO
Classic Uptown 1BR w\/ Fire Pits & Rooftop, nr L Red Line, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...
From $113 per night (USD)VRBO
- From $207 per night (USD)
VRBO
Barsala l Bright Studio with full kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Situated in Uptown Chicago, our modern and bright apartments are minutes away from countless options for dining and meet ...
From $207 per night (USD)VRBO
- From $493 per night (USD)
VRBO
PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by RedAwning
- 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 $493 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect for any type of traveler, my bright and inviting one bedroom condo in Uptown is a sanctuary stocked with every a ...
From $286 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Uptown studio apartment with breathing views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Incredible views from the rooftop, while taking a dip in the pool, gym washer and dryer, theater plus game room. Also it ...
From $175 per night (USD)VRBO
- From $182 per night (USD)
VRBO
Nice & Comfy Uptown Studio Apt near Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Welcome to our cozy and comfortable Uptown studio apartment, perfectly situated near some of Chicago's best dining and s ...
From $182 per night (USD)VRBO
- From $122 per night (USD)
VRBO
Convenient studio located in Buena Park (pet- friendly)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming unit located to the North of Boystown and 13 min walking distance to the big area of the Wrigleyfield. The st ...
From $122 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 $431 per night (USD)
VRBO
Elegant modern apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a lovely one bedroom with den and two bathrooms. Enjoy the English Garden in front or the very private patio off ...
From $431 per night (USD)VRBO
- From $846 per night (USD)
VRBO
Across From Wrigley Field, Beautiful 4 Bedroom
- 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 $846 per night (USD)VRBO
- From $1079 per night (USD)
VRBO
Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9
- 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 $1079 per night (USD)VRBO
- From $996 per night (USD)
VRBO
4 Bedroom 2 Bath in Wrigley Rooftop Building
- 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 $996 per night (USD)VRBO
- From $313 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 $313 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Cozy Lakeview apartment near Train Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Apartment is located in the charming Lakeview neighborhood steps away from the brown line train station, known for it's ...
From $153 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $957 per night (USD)
VRBO
Large Apt with 2 Car Garage and EV Charger! Walk to Wrigley Field & Brown Line!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
- Garage with 2 spots and EV charger just for you! - 10 Minute walk to Irving Park Brown Line Station - Desirable North ...
From $957 per night (USD)VRBO
- From $269 per night (USD)
VRBO
Spacious, Clean and Steps from Wrigley Field!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance fr ...
From $269 per night (USD)VRBO
- From $117 per night (USD)
VRBO
Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $117 per night (USD)VRBO
- From $353 per night (USD)
VRBO
Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lakeview. with balcony views over the city. It’ll be ea ...
From $353 per night (USD)VRBO
- From $99 per night (USD)
VRBO
Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $99 per night (USD)VRBO
- From $273 per night (USD)
VRBO
Cozy Garden Unit Located in North Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
My home is located on a charming tree-lined street in the North Center/Lakeview neighborhood. The featured space is a qu ...
From $273 per night (USD)VRBO
- Click For Pricing
VRBO
Custom 5 Bedrooms, Family Friendly, Centrally Located, WITH YARD and Parking!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
A beautiful 5 bedroom family home, located on the tree lined streets of Lakeview. A large, open-plan layout includes a 1 ...
Click For PricingVRBO
- From $150 per night (USD)
VRBO
Beautiful town house
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Beautiful town house sits in meticulously maintained courtyard with two private outdoor spaces. Freshly painted first f ...
From $150 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Fremont St. Guesthouse - Unit 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Classic Chicago Brownstone, updated 3 bedroom and 2 bathroom high end, 1st floor condo. Located on beautiful Fremont Str ...
From $323 per night (USD)VRBO
- From $187 per night (USD)
VRBO
Quiet Spacious 2BR Apt walk to Train, near Shops
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the ultimate comfort in this immaculate, tranquil, and fully furnished two-bedroom apartment located in a fam ...
From $187 per night (USD)VRBO
- From $90 per night (USD)
VRBO
Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Edgewater furnished one bedroom apartmen ...
From $90 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Edgewater furnished one bedroom apar ...
From $125 per night (USD)VRBO
- Click For Pricing
VRBO
Classic Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
Click For PricingVRBO
- From $244 per night (USD)
VRBO
Sophisticated 2BR Apt 5 mins Walk to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for the perfect place to stay during your visit to the Windy City? Our 2-bedroom apartment located just a short ...
From $244 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Modern 1BR Oasis in the Heart of the City
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for a beautifully furnished and well-equipped place to stay during your extended visit to Chicago? Look no furth ...
From $189 per night (USD)VRBO
- From $252 per night (USD)
VRBO
2-Bedroom Indulging Condo Apt in Festive Boystown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This stunning 2-bedroom apartment is situated just a few steps away from the tranquil Chicago Lake View, a beautiful tre ...
From $252 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Charming 1BR Apt in North Center Near Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our chic one-bedroom home, the perfect place to start your city adventures. This fully furnished apartment in ...
From $220 per night (USD)VRBO
- From $135 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 $135 per night (USD)VRBO
- From $89 per night (USD)
VRBO
Amazing Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Lakeview furnished one bedroom apartme ...
From $89 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Stunning Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Lakeview furnished one bedroom ...
From $130 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Wrigleyville Condo, 1\/2 block from Wrigley Field. Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Wrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown ...
From $359 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Spacious & Modern Family Friendly North Center Apt - Solar-Powered
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated, modern kitchen and bath, comfortable beds, and solar-powered. Great location in a safe neighborhood, Je ...
From $153 per night (USD)VRBO
- From $575 per night (USD)
VRBO
5 Bedroom Wrigleyville experience right by stadium
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Located on a peaceful side street of Wrigleyville, this private duplexed apartment is a unique blend of family friendly ...
From $575 per night (USD)VRBO
- From $244 per night (USD)
VRBO
Real Comfort in a 2BR APT close to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the vibrant city of Chicago! Experience the perfect home away from home in our stylish and fully furnished 2- ...
From $244 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Your 1BR Homey Haven in Vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the allure of urban living at its finest with a warm invitation to our exquisitely renovated one-bedroom apartm ...
From $237 per night (USD)VRBO
- Click For Pricing
VRBO
❤️ Modern 2BR Apt Right next to Wrigley Field & Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience city life; Located in Wrigley! Feel like a local! ✔️Right Next to Wrigley Field (1 block away); Home of Chi ...
Click For PricingVRBO
- From $325 per night (USD)
VRBO
Vintage Wrigley 1Br\/1Ba with parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Wrigleyville! 1 block from Wrigley field. Countless delicious restaurants, pubs and nightlife all right out ...
From $325 per night (USD)VRBO
- From $226 per night (USD)
VRBO
Roomy Lakeview 1BR w\/ W\/D, Gym, near Lakefront Trail, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $226 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Best Lincoln Square Location - Spacious 2 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming apartment in an updated 1800s beautiful brick building. Located in the heart of Chicago's Lincoln Square neighb ...
From $215 per night (USD)VRBO
- From $362 per night (USD)
VRBO
Wrigleyville Inn, Beautiful Modern 1 Bedroom, Steps from Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently built from the ground up and featured on the Travel Channel, you will love our beautifully furnished one-bedroo ...
From $362 per night (USD)VRBO
- From $568 per night (USD)
VRBO
Wrigleyville\/Boystown Basement Gem
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Please be aware: *Ceilings are LOW *Stairs to downstairs are STEEP *unit has very LITTLE NATURAL LIGHT This garden unit ...
From $568 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Penthouse Level, Stunning Wrigley Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully designed space for a modern stay, located in the heart of three amazing Chicago neighborhoods. Seated on a q ...
From $900 per night (USD)VRBO
- Click For Pricing
VRBO
Lakeview Greystone One Block From Wrigleyfield
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Chicago like a local with your own professionally cleaned apartment. Step into the rainfall shower for a refr ...
Click For PricingVRBO
- From $168 per night (USD)
VRBO
Retro Apartment in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full o ...
From $168 per night (USD)VRBO
- From $267 per night (USD)
VRBO
Modern Wrigley Oasis with Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Immerse yourself in the charm of Wrigley with this beautifully designed modern oasis, perfectly situated in the heart of ...
From $267 per night (USD)VRBO