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

Near North Side (Chicago) Rentals

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 $156 per night (USD)
VRBO
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)
VRBO
From $485 per night (USD)
Expedia
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)
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 $207 per night (USD)
VRBO
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)
VRBO
From $140 per night (USD)
Expedia
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)
Expedia
From $547 per night (USD)
VRBO
Captivating Corner PENTHOUSE w/ Lake and Skyline View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A property ideal for the upwardly mobile or traveling elite. This Stylish 2000 square-foot residence is a corner penthou ...
From $547 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 $419 per night (USD)
VRBO
Corner 3BR in Streeterville | Views | Roof Deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stunning 1,500+ square foot corner apartment with oversize windows, an open layout, and dramatic city and lake ...
From $419 per night (USD)
VRBO
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
Click For Pricing
Expedia
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
Expedia
From $124 per night (USD)
VRBO
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)
VRBO
From $218 per night (USD)
Expedia
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)
Expedia
From $244 per night (USD)
VRBO
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)
VRBO
From $149 per night (USD)
Expedia
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)
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 $487 per night (USD)
Expedia
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)
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 $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)
Expedia
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)
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 $200 per night (USD)
VRBO
Trendy Streeterville Studio w/ Pool & Gym, nr Navy Pier, 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 $200 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)
VRBO
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)
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 $89 per night (USD)
VRBO
Modern Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $89 per night (USD)
VRBO
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)
Expedia
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)
Expedia
From $315 per night (USD)
VRBO
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)
VRBO
Click For Pricing
Expedia
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
Expedia
From $484 per night (USD)
VRBO
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)
VRBO
From $106 per night (USD)
Expedia
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)
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 $388 per night (USD)
VRBO
Charming 2 BR apartment near Lincoln Park zoo in historic building
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $388 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 $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)
Expedia
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)
Expedia
From $423 per night (USD)
VRBO
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)
VRBO
From $195 per night (USD)
Expedia
Stylish Gold Coast 1BR w/ Grills & Gym, nr Shops & Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Gold Coast furnished one bedroom ap ...
From $195 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
From $197 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Free Breakfast, Near Water Tower Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $197 per night (USD)
VRBO
From $329 per night (USD)
VRBO
Making The Best Memories Along The Way! Free Breakfast, Pets Allowed
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $329 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
From $290 per night (USD)
VRBO
Just What You Were Looking For! Near Chicago Museum of Contemporary Art
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 $290 per night (USD)
VRBO
From $121 per night (USD)
VRBO
Vintage firehouse quiet two bedroom apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fully furnished updated 1880s horse and buggy firehouse carriage house that is clean quiet private and safe. Modern and ...
From $121 per night (USD)
VRBO
From $92 per night (USD)
Expedia
Sunny River North 1BR w/ Gym & Coffee Shop, nr L & Beach, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Near North furnished one bedroom apartm ...
From $92 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Ultimate City Life Experience in Heart of Chicago | 2 Family Ready Roos
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $264 per night (USD)
VRBO
From $138 per night (USD)
VRBO
Cozy Corner in Chicago’s Downtown| Walking Distance to Ohio Street Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 1200 sq. ft, equipped with complimentary toiletries, TV, avai ...
From $138 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Chicago Condo: Near Lincoln Park & DePaul!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover the best of Chicago at this charming 1-bedroom, 1-bath vacation rental in Lincoln Park! Whether you’re here for ...
From $295 per night (USD)
VRBO
From $381 per night (USD)
VRBO
jane's house a boutique historical flat in chicago - close to everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jane's house is a cozy 130 year old victorian Italianate remodeled into a modern open concept living space. Our unique ...
From $381 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Level Spacious one bedroom suite with king bed, walk-in closet, full kitchen.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $154 per night (USD)
VRBO
$Level River North Luxury Two Bedroom Suite\n$
From $261 per night (USD)
Expedia
Level River North Luxury Two Bedroom Suite\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $261 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Level River North - Spacious Executive Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $176 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Level - Fulton Market Junior Two Bedroom Two Bath suite with kitchen and balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $238 per night (USD)
Expedia
Click For Pricing
VRBO
Level - Old Town 3 Bedroom, 2 Bath spacious suite with full kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
Click For Pricing
VRBO
From $210 per night (USD)
Expedia
Level Old Town - Executive One Bedroom Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $210 per night (USD)
Expedia
$▌360° City Skyline Chicago ▌\n$
Click For Pricing
VRBO
▌360° City Skyline Chicago ▌\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
About this space It's rare to find a place that's both historic and one-of-a-kind. This 3 bedroom + 2.5 bath vacation re ...
Click For Pricing
VRBO
From $512 per night (USD)
VRBO
Gold Coast 3bed Penthouse w/ Private Terrace, Housekeeping, Laundry and Valet.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Furnished Terrace through tall glass doors from the Primary Suite on the second floor. Get all the comforts and ...
From $512 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Splendid Corner 3BR in the Loop | City Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $527 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Entire Condo and Parking at the heart of Wicker Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This is my cozy Bucktown / Wicker Park home. Wonderfully walkable (right on the border of both neighborhoods), with deli ...
From $204 per night (USD)
VRBO
From $1131 per night (USD)
VRBO
Designer-renovated house in the heart of Wicker Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Location, Style, and Comfort all in one place. We have just finished renovating our home after a full gut with all new b ...
From $1131 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Aparthotel with a fitness center, a short walk to Willis Tower This smoke-free aparthotel features a fitness center, con ...
From $169 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Stylish Streeterville 2BR w/ Lounge & Pool, nr Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $298 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Upscale Streeterville Jr 1BR w/ Gym, nr Magnificent Mile, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $215 per night (USD)
Expedia
From $109 per night (USD)
VRBO
Bright Streeterville Jr 1BR w/ Steam Room, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $109 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Luxe Streeterville 1BR w/ Lounge & Terrace, n Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this beautiful one bedroom Blueground apartment. You’ll love comin ...
From $164 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Airy Streeterville 1BR w/ Indoor Pool, close to Navy Pier, 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 $238 per night (USD)
VRBO
Click For Pricing
Expedia
Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Welcome to The Hubbard House. A Large yet Cozy 4 story, 4 bedroom home in the Fulton Market District. This beautifully ...
Click For Pricing
Expedia
From $896 per night (USD)
VRBO
Sophisticated Urban Escape, 4 Cozy Units, Near Water Tower Chicago!
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 $344 per night (USD)
VRBO
Boutique Charm, Modern Comforts, Near Field Museum of Natural History
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
From $447 per night (USD)
VRBO
Sleek Retreat, Unforgettable Experience, 2 Stylish Units Near 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 $672 per night (USD)
VRBO
Central Chic: 3 Plush Units, Near Chicago Museum of Contemporary Art!
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 $196 per night (USD)
VRBO
Chic Urban Oasis, Pet-Friendly Unit, Near The Art Institute of Chicago!
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 $196 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Central Serenity, Cityscape Views Close To Field Museum of Natural History!
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 $290 per night (USD)
VRBO

Search Your Destination Now!

Near North Side (Chicago) Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 623 Rentals