North Branch of the Chicago River, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in North Branch of the Chicago River, Illinois on RentalSaver.com!

North Branch of the Chicago River Rentals

From $209 per night (USD)
VRBO
Dreamy River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $209 per night (USD)
VRBO
From $472 per night (USD)
Expedia
Prime Downtown 2BR with Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Experience unparalleled convenience and luxury at 'The Kroc,' perfect for travelers seeking upscale urban livin ...
From $472 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Gold Coast Luxury: 2BR with Sweeping City Vistas
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Stay in 'The Addams,' a prime 2BR with skyline views and a balcony, ideal for those seeking a memorable Chicago ...
From $565 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Luxury 2BR near Millennium Park + 5-Star Reviews
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Ideal for travelers exploring the city, 'The Jones' blends historic charm with modern amenities, steps from top ...
From $468 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Uniquely Spacious Two-Story Loft in Wicker Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Perfect for bonding with family and friends! This one-of-a kind Loft offers a spacious open concept, connecting the livi ...
From $523 per night (USD)
VRBO
From $498 per night (USD)
Expedia
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
A beautiful modern 2450 sq feet apartment with a private rooftop deck, private patio and yard, brand new appliances, and ...
From $498 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Live Like a Local at the Beachwood Inn! Private Balcony Overlooking One of Chicago's Best New Restaurants by AllSet Turnover
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Located on the second floor of Ina Mae Tavern & Packaged Goods, one of Chicago's best new restaurants, the Beachwood In ...
From $186 per night (USD)
VRBO
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Expedia
Cabin 204 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
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Expedia
From $377 per night (USD)
VRBO
Converted Store Front Home Lets You Live Like a Local in the Heart of it All! by AllSet Turnover
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Two-level River West home great for travelers who want to see the best of Chicago (its neighborhoods!). The living room ...
From $377 per night (USD)
VRBO
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Expedia
Cabin 206 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
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Expedia
From $208 per night (USD)
VRBO
PET FRIENDLY and Room for 7! Large Common Areas to Converse and Connect by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
**Now hosting guests for stays 32 nights or longer** Staying in River West is the best way to see Chicago - plus you' ...
From $208 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Free Parking! Designed for Work and Play - Perfect for Any Traveler with 2 Work Spaces and Old Town Charm by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Plenty of space to spread out and relax! My two level townhome in the hot Old Town neighborhood makes for the perfect r ...
From $289 per night (USD)
Expedia
From $155 per night (USD)
VRBO
Cabin 201 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
From $155 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Cabin 106 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unique space set up to be ADA accessible with wide walkways, step-free shower, bathroom grab bars, and open space benea ...
From $144 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Cabin 301 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
From $159 per night (USD)
VRBO
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Expedia
Cabin 305 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
Click For Pricing
Expedia
From $303 per night (USD)
VRBO
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)
VRBO
From $149 per night (USD)
Expedia
Cabin 202 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
From $149 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Perfect 1BR in Lincoln Park - Steps to DePaul! by AllSet Turnover
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming garden unit in Lincoln Park is ideally situated for any type of traveler! There are plenty of parks, dini ...
From $165 per night (USD)
VRBO
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Expedia
Cabin 205 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
Click For Pricing
Expedia
From $136 per night (USD)
VRBO
Cabin 303 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
From $136 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Top Floor in the Heart of West Town! Perfect for Any Group and PET FRIENDLY! by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
**Hosting 32+ Night Reservations** Spacious top-floor 2-bedroom duplex in the heart of Chicago's hot West Town! Easi ...
From $140 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Take the Whole Crew Out to the Ballgame! Four Bedrooms and Only 1 Mile from Wrigley by AllSet Turnover
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Prime location in Lakeview, steps from the Southport Corridor, only one mile from Wrigley! My fantastic four bedroom ap ...
From $405 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Cabin 101 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot W ...
From $156 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Our two-story Old Town condo is a great place for all travelers to experience our favorite neighborhood in Chicago! Enj ...
From $485 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 $125 per night (USD)
VRBO
Sleek Loop Studio w/ Pool, Gym & Lounge, near Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish studio Blueground apartment. You’ll love coming home ...
From $125 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Upscale West Loop 1BR w/ W/D, Gym & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in West Loop with high floor views over the city. It’ll be ...
From $190 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Free Parking & Wifi in Bucktown/Logan Square Apt, Close to Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Recently Renovated and Redesigned, you may not even want to leave the unit and area! Enjoy a Stylish experience at a cen ...
From $228 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Ideal Gold Coast 1BR w/ Gym & Lounge, 1 block 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 $207 per night (USD)
Expedia
From $140 per night (USD)
VRBO
Bright Loop 1BR w/ Gym & Doorman, nr L & Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $140 per night (USD)
VRBO
From $100 per night (USD)
Expedia
Trendy River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish River North furnished one bedroom apa ...
From $100 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Luxe River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, 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 $169 per night (USD)
VRBO
From $727 per night (USD)
Expedia
Stunning / Spacious 6BD Home + garage - Bucktown!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
About this space NEW HOME/NEWLY FURNISHED! This 5 br home / 6beds is centrally located to Chicago's best areas; Wicker P ...
From $727 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Roomy Streeterville 2BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Streeterville furnished two bed ...
From $407 per night (USD)
VRBO
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Expedia
Stylish Designer Apartment near DePaul - Lincoln Park
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A design lover's dream! Spend your next trip to Chicago in a beautifully remodeled 4 bedroom, 3.5 bath apartment in Linc ...
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Expedia
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VRBO
Sleek Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Chicago Loop furnished one bedroom apa ...
Click For Pricing
VRBO
From $124 per night (USD)
Expedia
Urban West Loop 1BR w/ Gym, Pool, nr. Fulton Market, 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 $124 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Ideal River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $218 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Amazing Loop Studio w/ Pool & Gym, steps to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Chicago Loop furnished one bedroom ...
From $244 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Sunlit Streeterville 1BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with views over the city. It’ll be easy t ...
From $149 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Light and bright 3BD duplex in Avondale, Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ahh, the calm colors and neutral tones in this main & upper level, 3 bedroom / 2 bath duplex is just what you need to re ...
From $204 per night (USD)
Expedia
From $285 per night (USD)
VRBO
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $285 per night (USD)
VRBO
From $893 per night (USD)
Expedia
870 1&2 - 2 Separate Suites in same building
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Summary: You will get 2 separate Suites that are directly next to each other. Each Suite has 2 bedrooms and 2 bathrooms. ...
From $893 per night (USD)
Expedia
From $323 per night (USD)
VRBO
PET FRIENDLY! Historic River West Neighborhood - Easy Access to O'Hare by AllSet Turnover
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover Urban Living in this spacious 3-bed, 2-bath condo nestled in the vibrant River West neighborhood. Flooded with ...
From $323 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Avondale Condo Near Classic Bars, Eateries, and More! by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Start your adventures in our updated firefighter-themed 3 bedroom 1 bath condo in Chicago's Avondale neighborhood. Bold ...
From $245 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Beautiful, Remodeled Penthouse Unit in Old Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Summary: This newly remodeled, Penthouse unit is the perfect place to enjoy the city and come back to a space that is re ...
From $487 per night (USD)
VRBO
From $293 per night (USD)
Expedia
The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CITY OF CHICAGO VACATION RENTAL LICENSE #2246788 We have been operating as a professionally managed vacation rental sin ...
From $293 per night (USD)
Expedia
From $109 per night (USD)
VRBO
MTM Fully Furnished Rental in Old Town - 2 beds
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Looking for a month to month fully furnished rental that is move in ready? - ALL utilities, WIFI, Cable 100% ...
From $109 per night (USD)
VRBO
From $114 per night (USD)
Expedia
MTM Fully Furnished Rental in Old Town - 2 beds
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Looking for a month to month fully furnished rental that is move in ready? - ALL utilities, WIFI, Cable 100% r ...
From $114 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Upgraded luxury and spacious Living in this beautiful walkable, and safe Roscoe Village/Wrigley field, surrounded by sho ...
From $307 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Your Chicago Tropical Oasis in the Heart of Wicker Park!
Bedrooms:
2
Bathrooms:
5
Sleeps:
23
Feel those tropical feels in our sprawling 5 bedroom space in the heart of Wicker Park that comfortably sleeps up to 23 ...
From $205 per night (USD)
VRBO
From $111 per night (USD)
VRBO
Stunning Suite 4 @ Hotel Nemo Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...
From $111 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Fulton House #2 (2bd/ 1ba)
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Min 1 month stay - Unique & stylishly designed, this highly sought after location is for those that want to sta ...
From $194 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Brand-New Building! Secure and Stylish - Great River West Location! by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy Urban Living in my 2 bed 2 bath River West apartment. Located in a beautiful and secure new building, relax in a ...
From $264 per night (USD)
VRBO
From $797 per night (USD)
Expedia
The Exclusive- 7 Bed, 6 Bath Retreat
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
This brand new home located in Wicker Park offers 7 beds, 6 baths, 2 living areas, 2 chef's kitchen and a dedicated dini ...
From $797 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Spacious Downtown Chicago Condo with Spa Bath, King Bed, Patio, 3 Blocks to L
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore Chicago's charm just moments from downtown! This vacation rental boasts a spa bath with a luxurious rain shower ...
From $324 per night (USD)
VRBO
From $212 per night (USD)
Expedia
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
"Step into the vibrant heart of River North, where your window frames forever views and the sky blushes with the best s ...
From $212 per night (USD)
Expedia
From $354 per night (USD)
VRBO
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
You will be transported when you stay with us in this hip and charming space in Chicago's most vibrant neighborhood! Enj ...
From $354 per night (USD)
VRBO
From $369 per night (USD)
VRBO
Steps from the “L” train to Wrigley & Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a beautiful space with lots of natural light located on the top (2nd) floor. Stainless steel appliances includin ...
From $369 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Chic Corner 2BR in the Loop | City & Lake Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and lovely city and l ...
From $419 per night (USD)
VRBO
From $584 per night (USD)
Expedia
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/ente ...
From $584 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spacious 4 bed 3 bath pet friendly duplex up lives like a house with everything you need and want. Great neighborhood pa ...
From $624 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Premium Loop 1BR w/ Roof, Gym & Lounge, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished one bedroom a ...
From $214 per night (USD)
Expedia
From $255 per night (USD)
VRBO
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $255 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $294 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Sew u wana stay in a storefront?
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
If you're staying in Chicago and want to experience Wicker Park, you gotta stay in a space as unique as the neighborhood ...
From $243 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Central Chicago Suite2 Access to Patio!
Bedrooms:
1
Bathrooms:
2
Sleeps:
9
Summary: Experience what Chicago has to offer and stay at our Luxury Chicago Suite! Perfect for your Chicago visit! The ...
From $315 per night (USD)
Expedia
Click For Pricing
VRBO
4BD Condo w/Parking & Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious 4-bedroom, 2.5-bathroom condo unit that's perfect for your stay in Chicago. This stunning unit ...
Click For Pricing
VRBO
From $484 per night (USD)
Expedia
Spacious 2BR in The Loop + 5-Star Comfort
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Cooke' is your ideal base for exploring Chicago's vibrant attractions, promising a luxurious stay with uni ...
From $484 per night (USD)
Expedia
From $106 per night (USD)
VRBO
Gorgeous West Loop 1BR w/ Deck, Pool & Gym, 3 blocks to L, 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 $106 per night (USD)
VRBO
From $794 per night (USD)
Expedia
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)
Expedia
From $408 per night (USD)
VRBO
Penthouse Escape + Vibrant West Loop Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Discover 'The Fitz,' a designer 3BR penthouse ideal for your Chicago getaway, with top marks for cleanliness an ...
From $408 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Stunning Duplex-4BD/3BA *Prime Location* Sleeps 12
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This Wicker Park BNB location has it ALL! This prime location gives our guests access to restaurants, shops, and Chicago ...
From $409 per night (USD)
Expedia
From $1437 per night (USD)
VRBO
River West 3BR Penthouse Duo: Skyline Comfort
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: Ideal for groups seeking spacious elegance and stunning views at 'The Kane.' Rated 5-stars in cleanliness, ac ...
From $1437 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Scenic 3BR PH for Tourism + Prime Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: At 'The Bow,' enjoy stunning city views and spacious comfort for your Chicago getaway. It's a guest-approved ...
From $466 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Rooftop, West Loop Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Very spacious unit over a boutique shop. No other tenants in the building with your very own private rooftop de ...
From $270 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Discover the Best of Chicago's Loop Near Ford Center Theatre! Pets are Welcome!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $201 per night (USD)
VRBO
From $1681 per night (USD)
VRBO
3 Prime 2BR Units + Ideal Business Retreat
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
Summary: Elevate your group experience at 'The Jordan', ideally located near Millennium Park. 100% 5-star reviews sinc ...
From $1681 per night (USD)
VRBO
From $2078 per night (USD)
VRBO
Prime Loop Apts + Convenience for Groups
Bedrooms:
8
Bathrooms:
8
Sleeps:
20
Summary: The premier choice for large group and family stays, 'The Crawford' offers four modern apartments in the heart ...
From $2078 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Spacious 3-bedroom Duplex condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bring the whole family to this great place with lots of room for fun. Spacious and cozy with lots of light in this corne ...
From $247 per night (USD)
VRBO
From $254 per night (USD)
Expedia
WickerPark 2Bdrm near Downtown,SaltShed Jack’s Pumpkin PopUp 159.00 Oct 15-17
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
10 minutes from downtown, the Salt Shed and Lincoln Park! Seek comfort in this Wicker Park Urban Sanctuary close to Down ...
From $254 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Luxury Designer Penthouse Loft | Sleeps 20
Bedrooms:
3
Bathrooms:
4
Sleeps:
20
Summary: BRAND NEW DESIGNER PENTHOUSE LOFT IN WICKER PARK! Sleeps up to 20 people! Enjoy your own private loft in Chic ...
From $674 per night (USD)
VRBO
From $355 per night (USD)
Expedia
The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This is a legally licensed Chicago vacation rental. We have been operating as a professionally managed vacation rental ...
From $355 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $211 per night (USD)
VRBO
From $552 per night (USD)
VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, Pet-Friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $552 per night (USD)
VRBO
From $226 per night (USD)
VRBO
REMODELED Splendid Flat in Bucktown +Back Porch, Ranked GUEST FAVORITE! Pets OK!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Flat remodeled in May 2025 - with brand new floors & refreshed with new colors! Cute & cozy 2-bedroom flat w/sofa sleepe ...
From $226 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Beautiful Downtown 3BR with Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
A beautiful and modern three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'l ...
From $423 per night (USD)
Expedia
From $264 per night (USD)
VRBO
2bd River North Condo with Million Dollar Views! by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
32+ NIGHTS MIN, *1 GARAGE PARKING SPACE INCL* Experience our stunning 49th floor River North condo! With 2 bedrooms & ...
From $264 per night (USD)
VRBO
Click For Pricing
Expedia
Aloha 2.0 - Teal Bedroom
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Feel those tropical feels in our sprawling space in the heart of Wicker Park. Flamingos, marlins, and sharks combined wi ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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
VRBO
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)
VRBO
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)
VRBO
From $434 per night (USD)
VRBO
Chic River North Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our Chic River North Retreat, a hidden gem in vibrant River North, Chicago. Discover a rare 2-bedroo ...
From $434 per night (USD)
VRBO
From $896 per night (USD)
VRBO
Ideal Mix of Comfort and Value! 4 Comfortable Units, Near Ohio Street Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Experience the Windy City's elegance & charm from our central, downtown location This listing is for 4 separate rooms w ...
From $896 per night (USD)
VRBO
From $672 per night (USD)
VRBO
Make Your Trip More Enjoyable! 3 Relaxing Units, Near Art Institute of Chicago
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Experience the Windy City's elegance & charm from our central, downtown location This listing is for 3 separate rooms w ...
From $672 per night (USD)
VRBO
From $447 per night (USD)
VRBO
Home Away From Home! 2 Modern Units, Close to Willis Tower
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Experience the Windy City's elegance & charm from our central, downtown location This listing is for 2 separate rooms w ...
From $447 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Always a Great Idea To Unwind! Near Field Museum of Natural History
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $229 per night (USD)
VRBO
From $224 per night (USD)
VRBO
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $224 per night (USD)
VRBO
From $344 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! Near Buckingham Memorial Fountain, Pets are Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $344 per night (USD)
VRBO

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