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

$▌360° City Skyline Chicago ▌\n$
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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 ...
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VRBO
From $215 per night (USD)
Expedia
Bucktown Condo Just Two Blocks from the L by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of ameniti ...
From $215 per night (USD)
Expedia
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 $93 per night (USD)
Expedia
Terrific Loop 1BR w/ Gym & Roof Deck, nr Millennium Park, 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 $93 per night (USD)
Expedia
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 $193 per night (USD)
Expedia
Cozy East Village Apt
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Our cozy open area Fully Furnished unit features two bedrooms, two baths, in-unit laundry, a fully equipped kitchen, you ...
From $193 per night (USD)
Expedia
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VRBO
*BRAND NEW* Luxury Apt in Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience Chicago in a newly built high-rise with stunning views, amenities, and unmatched comfort. The Unit: - Lightn ...
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VRBO
From $343 per night (USD)
Expedia
Trendy Wicker Park Loft with Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in trendy Wicker Park, our modern Chicago loft boasts open-plan living, exposed brickwork and plenty of room to ...
From $343 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Spacious Wicker Park Hideaway with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly rehabbed and designed 3 bedroom, 2 bath is centrally located in the trendy Wicker Park neighborhood. You can ...
From $262 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Located in the Heart of Lincoln Park, walking distance to North Ave beach & more
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our 3-level townhouse is the perfect space for those relocating, traveling for work, or in town for more extended visits ...
From $204 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
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
From $201 per night (USD)
VRBO
Elegant Stay: Plush Unit With City Views, Close To Water Tower 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 $201 per night (USD)
VRBO
From $224 per night (USD)
VRBO
Stay in Luxury Downtown! Pet-Friendly, Fitness Center!
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 $229 per night (USD)
VRBO
Luxury Boutique, Prime Spot, Pet-Friendly Unit!
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
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VRBO
Light n' Bright City Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Find your home away from home at this peaceful and centrally-located condo. A perfect place to linger and explore Chicag ...
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VRBO
From $487 per night (USD)
Expedia
Luxe Penthouse with Home Theater and Amazing Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning luxe penthouse in the heart of the East Village. This property has it all. Two master suites with attached bath ...
From $487 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Upscale Penthouse Private Balconies Amazing Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
My place is conveniently located in East Village, situated between the cultural hubs of Wicker Park and West Town & not ...
From $231 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Deluxe River West PH for Unforgettable Memories
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: 'The Arc' impresses tourists with stunning city vistas and spacious design from a prime location. 94% of revie ...
From $513 per night (USD)
Expedia
From $570 per night (USD)
VRBO
4 Bedroom Penthouse Loft in Heart of Wicker Park with Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
This vintage 4 bedroom loft can allocate up to 14 people and is located on a busy commercial street in the heart of Wick ...
From $570 per night (USD)
VRBO
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Expedia
Professional Hotel - Short distance to the AHR Expo
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
Rental would be perfect for the Annual AHR Expo at McCormick. The event for HVACR Manufacturers. Hotel Blake is a short ...
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Expedia
$Good Ol' Greystone, A Genuine Chicago Experience\n\n$
From $211 per night (USD)
VRBO
Good Ol' Greystone, A Genuine Chicago Experience\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to the charming Good Ol' Greystone, located in the vibrant heart of Wicker Park, one of Chicago's trendiest neig ...
From $211 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Sky-High 3BR Penthouse in West Loop
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Go the extra mile for your Chicago getaway at 'The Mile.' Located in the vibrant West Loop, this home offers ...
From $408 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Luxe 1BR: Unmatched Views & Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Experience vibrant River West from 'The Hue,' a premium 1BR designed for young professionals and city explorers ...
From $318 per night (USD)
VRBO
From $576 per night (USD)
Expedia
GROUP LUX LINCOLN PARK 4BD/4.5BA Home +parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Escape into this Lincoln Park Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retai ...
From $576 per night (USD)
Expedia
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VRBO
Chicago Shared Living Space with Office Space
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Our space is fully furnished with a co-living experience. You will be staying in Rm 1 (first room on the left) in an apa ...
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VRBO
From $536 per night (USD)
Expedia
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Feel at Home, Unwind, and Enjoy the amenities you deserve at our 3bed 2-Story Penthouse. Most homes don’t provide profe ...
From $536 per night (USD)
Expedia
From $445 per night (USD)
VRBO
West Loop 2BR with Skyline Views + Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Experience sweeping Chicago skyline views at 'The Lincoln,' a vibrant city escape backed by a strong 80%+ 5-sta ...
From $445 per night (USD)
VRBO
From $1437 per night (USD)
VRBO
Luxury 3BR Penthouses + Group Comfort Awaits
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: The ultimate destination for your group's getaway, 'The Prism' offers a unique collection of two 3BR penthouses ...
From $1437 per night (USD)
VRBO
From $1459 per night (USD)
VRBO
Skyline View Duo for Groups: Unmatched Luxury Stay
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Summary: Discover 'The Seven,' an exclusive offering of two same-floor penthouses designed to provide your group with a ...
From $1459 per night (USD)
VRBO
From $2180 per night (USD)
VRBO
3 Penthouses, 1 Floor, Group Stay, Sleeps 21
Bedrooms:
8
Bathrooms:
9
Sleeps:
21
Summary: Ideal for discerning business travelers, 'The Marvelo' features three luxurious 3BR penthouses, each offering b ...
From $2180 per night (USD)
VRBO
From $1486 per night (USD)
VRBO
Spacious Penthouse Trio + Skyline Views for Groups
Bedrooms:
7
Bathrooms:
9
Sleeps:
22
Summary: For an iconic Chicago stay, 'The Bean' provides three stunning penthouses for your family or business gathering ...
From $1486 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Top of River West: Luxe Penthouse for Groups
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: 'The Iris' offers breathtaking skyline views and premium amenities, perfect for travelers seeking a memorable u ...
From $474 per night (USD)
Expedia
From $254 per night (USD)
VRBO
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)
VRBO
From $674 per night (USD)
Expedia
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)
Expedia
From $831 per night (USD)
VRBO
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
5-stories River West townhouse with 4 queen beds and 3 en-suite full bathrooms. No powder rooms! Standout features inclu ...
From $831 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 $140 per night (USD)
VRBO
Cabin 105 by 747 Lofts
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
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 $140 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 $403 per night (USD)
VRBO
Level - Fulton market Spacious 3 bedroom 2 baths with luxury kitchen and balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $403 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Level - Fulton Market One Bedroom Suite with full kitchen and living room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $201 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Level - Fulton market Modern two bedroom two bath with full 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 $278 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $157 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Level - Fulton Market spacious 2 bedroom, 2 bath suite with full kitchen
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 $326 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
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)
Expedia
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)
Expedia
From $282 per night (USD)
VRBO
Remodeled 3 story entire townhouse available in the heart of Lincoln Park.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Welcome to our urban oasis in Lincoln Park! Offering the entire townhouse available for your stay. The space offers 3 pr ...
From $282 per night (USD)
VRBO
From $281 per night (USD)
VRBO
WickerPark 2Bdrm Downtown SaltShed Jack’s Pumpkin PopUp Sale 159.00 Oct 20-24
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Find comfort in this Urban Sanctuary!10 min. to Downtown & Salt Shed. Enjoy the art galleries on Chicago Ave and the Bou ...
From $281 per night (USD)
VRBO
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VRBO
1-Bedroom Suite at a 4.5⭐️ Hotel
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Luxurious grey, metallic, and powder blue decor gives this sophisticated One Bedroom Suite the feeling of a peaceful ret ...
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VRBO
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Expedia
1-Bedroom Suite at a 4.5⭐️ Hotel
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A beautiful hotel with flawlessly elegant decor. Boasting the ambiance of a bespoke boutique, the Kimpton is located in ...
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Expedia
From $327 per night (USD)
VRBO
Bucktown Private Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your peaceful urban retreat, nestled in the heart of vibrant Chicago! This stylishly furnished, sunlit apartm ...
From $327 per night (USD)
VRBO
From $147 per night (USD)
VRBO
Luxury Extended-Stay 1BR in West Loop for Professionals and Interns
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Live like a local in this **bright, 720 sq ft 1BR apartment** nestled in Fulton Market’s hottest district. Designed for ...
From $147 per night (USD)
VRBO
From $568 per night (USD)
VRBO
NEW 4BR Designer Flat in Wicker Park/Bucktown
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
We invite you to spend your next trip in this beautifully remodeled flat in Chicago's iconic Wicker Park neighborhood. S ...
From $568 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Downtown Goose Island with access to patio - 1
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 $319 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Designer 3BR Penthouse l Private Patio l Rooftop l Gym l 5-Star Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Live the high life in this stunning 3BR penthouse featuring a private terrace, gym, and access to a rooftop with panoram ...
From $408 per night (USD)
VRBO
From $545 per night (USD)
Expedia
LUX 3-Level Chicago Home +garage & patio
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Escape into our new, 3,300 sq ft, Boho-styled home! Guests love this home because: - Steps away from top-notch restaur ...
From $545 per night (USD)
Expedia
Click For Pricing
VRBO
FESTIVE GRAFITTI POP-ART 3BR - Wicker Park - Ukrainian Village
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of dow ...
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VRBO
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Expedia
CELEBRATE CHICAGO VIBE - 3BR - Adventures Await - Bucktown - Wicker Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows. The place is kept clean, tidy, ...
Click For Pricing
Expedia
From $590 per night (USD)
VRBO
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
**Private Gated Parking for 3 Cars Included You'll love staying at our beautifully designed duplex up plus additional ...
From $590 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Spacious 2 Bedroom unit with a Free Parking Spot
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2-bedroom unit with large living room, comfortable sofa beds is in the 3 floor building owned by 3 sisters. 6 peopl ...
From $681 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Flexhome Ukrainian Village 2BR D1
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Please review the House Rules before booking as we reserve the right to end the stay if violated: 1. No parties, gath ...
From $166 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Flexhome East Village 2BR H1
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The space: The apartment sleeps up to 4 with a comfy queen bed in each room plus flexible seating areas so you can work ...
From $173 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Hip West Loop 1BR w/ Gym, near Fulton Market & I-90, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District. It’ll be easy to simply show up ...
From $225 per night (USD)
VRBO
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Expedia
Cozy Billards Home w/ Spa Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
ndulge in luxury at our spacious Chicago retreat! Located in a vibrant neighborhood near parks, dining, and public trans ...
Click For Pricing
Expedia
From $158 per night (USD)
VRBO
Luxe River West 3BR w/ Pool, Gym, Pet Area, A/C & Rooftop, by Blueground
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the best of Chicago, with this three bedroom apartment in River West with views over the city. It’ll be easy to ...
From $158 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Blueground | The Loop, pool & gym, nr park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Chicago Loop furnished one bedroom ap ...
From $221 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Blueground | The Loop, pool & gym, nr park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Chicago Loop furnished one bedroom apar ...
From $203 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Charming 3-bedroom house in marvelous Ukrainian village Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to this charming house in Chicago.Located in Ukrainian village around bars, restaurants and supermarkets. Amazin ...
From $464 per night (USD)
Expedia
From $122 per night (USD)
VRBO
Chic 3 bedroom updated and vintage apt with WiFi in a Chicago 1880s firehouse
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Get ready to relax in this 3-bedroom apartment in Chicago. This fantastic property on the top floor of a two story build ...
From $122 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Nestled in the heart of Chicago, this delightful apartment offers a tranquil escape for guests. With a cozy bedroom feat ...
From $255 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Modern 1-bedroom apartment with 1 FREE Parking, Whirlpool bathtub,Full Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This welcoming 1-bedroom apartment in Chicago is perfect for your escape to the city. The space features a cozy queen be ...
From $633 per night (USD)
VRBO
Click For Pricing
Expedia
Bright, Cozy Apartment by Downtown & Train Stop; Great for Couples/Small Groups
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
No reviews of this unit yet but can see all of my other 5-star reviews here: vrbo/1397667 I have my comfy & cozy apartm ...
Click For Pricing
Expedia
From $282 per night (USD)
VRBO
Heart of Lincoln park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Charming 2BR in the Heart of Lincoln Park! Stay in the perfect Chicago location! This cozy 2-bedroom, 1-bathroom apartm ...
From $282 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Chic 2-bedroom with AC, WiFi, in terrific Chicago neighborhood of Wicker Park.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rainbow Rentals is delightful to offer this 2-bedroom gem in Chicago’s most vibrant and cool neighborhood of Wicker Park ...
From $136 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Blueground | West Loop, gym & bbq, nr Willis Tower
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely West Loop Gate furnished one bedroom a ...
From $92 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Chicago-Themed Apartment in West Town, Close to transportation and shops.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Chicago, enjoy what this 2-bedroom condo has to offer. With 1 queen bed and 1 full bed, this marvelous proper ...
From $169 per night (USD)
Expedia
From $189 per night (USD)
VRBO
La Quinta – Downtown King Conference Suite with Meeting Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Centrally located near top attractions and corporate offices, La Quinta offers business-friendly amenities in the heart ...
From $189 per night (USD)
VRBO
From $134 per night (USD)
VRBO
La Quinta – Double Bed Room Overlooking Quiet Courtyard Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just steps from the Willis Tower, Riverwalk, and the Loop’s financial district, La Quinta Chicago Downtown offers a conv ...
From $134 per night (USD)
VRBO
From $191 per night (USD)
VRBO
La Quinta – Deluxe King Room with City Views in Chicago Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Surrounded by iconic architecture and vibrant dining, La Quinta Chicago offers city access and skyline views in the Loop ...
From $191 per night (USD)
VRBO
From $165 per night (USD)
VRBO
La Quinta – Spacious Deluxe King Room in Prime Loop Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the heart of the Loop near Riverwalk and Millennium Park, La Quinta offers comfort and convenience for both w ...
From $165 per night (USD)
VRBO
From $150 per night (USD)
VRBO
La Quinta – Comfortable King Room in Downtown Chicago Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
From river cruises to museum strolls, La Quinta Chicago puts you minutes from the city's top sights and transit lines. T ...
From $150 per night (USD)
VRBO
From $189 per night (USD)
VRBO
La Quinta – King Suite with Living Area Near Chicago Landmarks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just off Wacker Drive, La Quinta provides easy access to Union Station and the Magnificent Mile. This non-smoking king s ...
From $189 per night (USD)
VRBO
From $160 per night (USD)
VRBO
La Quinta – 2 Queen Beds Room in Walkable Downtown Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $160 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Convenient Stay | 2 Pet-friendly Rooms Near Willis Tower and Skydeck
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $317 per night (USD)
VRBO
From $769 per night (USD)
VRBO
Entire Home in Lincoln Park - Amazing Game Room - Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This amazing single-family home in the heart of Lincoln Park is steps to popular restaurants and bars, upscale boutiques ...
From $769 per night (USD)
VRBO
From $449 per night (USD)
VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $449 per night (USD)
VRBO
From $5759 per night (USD)
VRBO
Your Own 8 Bedroom Private Inn and Event Space, Urban Garden Included
Bedrooms:
8
Bathrooms:
8
Sleeps:
16
Welcome to the Ruby Room, where staying is more than just lodging – it's an experience unlike any other. Whether you'r ...
From $5759 per night (USD)
VRBO
From $1677 per night (USD)
VRBO
New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21
Bedrooms:
4
Bathrooms:
6
Sleeps:
21
Perfect for groups and families! Welcome to our massive 6-bedroom Bucktown Wicker Park haven! • Unbeatable location i ...
From $1677 per night (USD)
VRBO

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