North Branch of the Chicago River Rentals
From $210 per night (USD)VRBO
Entire city apartment with free street parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly furnished and remodeled apartment unit with brand new appliances! We offer a smart TV, newly purchased mattress an ...
From $210 per night (USD)VRBO
From $204 per night (USD)VRBO
Elegant King Bed 1.5 Bath Suite in the Heart of Chicago's Gold Coast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each apartment offers a luxurious living experience, as they come fully furnished with all the amenities you could need. ...
From $204 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
From $414 per night (USD)VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...
From $414 per night (USD)VRBO
From $2368 per night (USD)VRBO
870 bldg - 3 Separate Suites in same building
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: This listing is ideal for LARGE GROUPS that wish to have individual Suites and separate living spaces for diffe ...
From $2368 per night (USD)VRBO
From $306 per night (USD)Expedia
Fulton market / Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...
From $306 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 $190 per night (USD)VRBO
Chicago Cityview Chic - Gold Coast/River North
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our stylish, modern 2-bed, 1-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover ...
From $190 per night (USD)VRBO
From $225 per night (USD)Expedia
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)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 $102 per night (USD)Expedia
Modern 2BR in Roscoe/Wrigley with Free Street Parking walk to Paulina Brown-line
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Desired longer stay in this beautiful, safe Roscoe Village/Lake View, surrounded by shops and restaurants. A ground-leve ...
From $102 per night (USD)Expedia
From $759 per night (USD)VRBO
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $759 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
From $196 per night (USD)VRBO
Downtown Delight: Chic Stay near Chicago Theater! 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 $196 per night (USD)VRBO
From $196 per night (USD)VRBO
Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
- 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 $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 $230 per night (USD)Expedia
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined str ...
From $230 per night (USD)Expedia
From $158 per night (USD)VRBO
Historic and Unique Brownstone in Gold Coast - 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...
From $158 per night (USD)VRBO
From $322 per night (USD)Expedia
3rd Floor Flat in River North - 3N
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Summary: REMODELED AND BUILT SPECIFICALLY FOR AIRBNB. The entire property is designed by a famous Chicago Designer us ...
From $322 per night (USD)Expedia
From $532 per night (USD)VRBO
Beautiful Unit CHI in Prime River North - 1
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This is a super unique place! This Downtown Living destination is perfect for everything from families with sma ...
From $532 per night (USD)VRBO
From $439 per night (USD)VRBO
Charming 4BR Coach House in River West Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning 4-bedroom retreat nestled in the heart of Chicago, where urban excitement meets modern ...
From $439 per night (USD)VRBO
From $586 per night (USD)VRBO
Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $586 per night (USD)VRBO
From $181 per night (USD)Expedia
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Feel comfortable in this spacious and unique 1bd space. New In-law-suite which includes a large family room. There is an ...
From $181 per night (USD)Expedia
From $308 per night (USD)VRBO
The Roscoe Village Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in a village within the city of Chicago, welcome to "The Roscoe Village Guesthouse", at the corner of Roscoe and ...
From $308 per night (USD)VRBO
From $244 per night (USD)Expedia
Deluxe River North 1BR w/ Gym, Pool & 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 charming River North furnished one bedroom ap ...
From $244 per night (USD)Expedia
From $151 per night (USD)VRBO
2BD/1 BA with summer patio in quiet Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $151 per night (USD)VRBO
From $283 per night (USD)Expedia
2-bedroom apartment just 2 minutes drive to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $283 per night (USD)Expedia
From $486 per night (USD)VRBO
3BR Luxury Modern Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most ...
From $486 per night (USD)VRBO
Click For PricingExpedia
Charming Village in the City
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About this space European style first floor apartment in a charming three story home built in 1910. Newly renovated with ...
Click For PricingExpedia
From $714 per night (USD)VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
✨ I highly recommend this location. The home is beautiful and quaint. The location is perfect. The neighbor is very quie ...
From $714 per night (USD)VRBO
From $205 per night (USD)Expedia
Suite 2 on Southport 4 Queen Beds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $205 per night (USD)Expedia
From $284 per night (USD)VRBO
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in the stylish two-bedroom apt on Beach Street, a street in Chicago. The city is full of award-winning restaurant ...
From $284 per night (USD)VRBO
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 $269 per night (USD)VRBO
Chicago Cityview Chic II Gold Coast/River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...
From $269 per night (USD)VRBO
From $144 per night (USD)Expedia
Neat Old Town 1BR Gym, W/D, Rooftop, BBQ & A/C, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Old Town furnished one bedroom ...
From $144 per night (USD)Expedia
From $479 per night (USD)VRBO
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience luxurious living in Chicago! This brand new, spacious 2-bedroom 2-bath penthouse apartment offers an ...
From $479 per night (USD)VRBO
From $803 per night (USD)Expedia
Rainbow Guest House: Charming 3-bedroom house in great location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Your Chicago adventure begins at this 3-bedroom house. Welcome to Rainbow Guest House. This designer owned, rebuilt and ...
From $803 per night (USD)Expedia
Click For PricingVRBO
Large Modern 2BD/2BA Condo in River North- Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our chic 2 bedroom, 2 bath condo (Parking Included) in the heart of River North, one of the most sought-after ...
Click For PricingVRBO
From $747 per night (USD)Expedia
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $747 per night (USD)Expedia
From $257 per night (USD)VRBO
Suite Dreams • Designer Style • Central • Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Stylish Home Base in Pilsen: Modern 3BR/2BA condo located in the vibrant East Pilsen/University Village ...
From $257 per night (USD)VRBO
From $271 per night (USD)Expedia
Charming 3-bedroom house with AC and WiFi in awesome Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Chicago retreat. This charming house offers all the comforts you need for a wond ...
From $271 per night (USD)Expedia
From $474 per night (USD)VRBO
West Loop PH: Unmatched Views & Private Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Ideal for families and business travelers seeking spacious luxury in Chicago's West Loop. Our last five guest ...
From $474 per night (USD)VRBO
From $533 per night (USD)Expedia
Explore Fulton Market + Retreat in Modern Comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience the vibrant heart of Fulton Market at 'The Neo', ideal for sophisticated travelers seeking scenic vi ...
From $533 per night (USD)Expedia
From $530 per night (USD)VRBO
Stylish 2BR Retreat in Fulton Market for Getaways
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience the perfect blend of design and location at 'The Deco', ideal for sophisticated travelers seeking le ...
From $530 per night (USD)VRBO
From $729 per night (USD)Expedia
Exclusive 3BR with Views, Ideal for Tourists
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 'The Rose' offers spacious urban living, steps from Millennium Park. With 90% of our reviews at 5 stars since 2 ...
From $729 per night (USD)Expedia
From $392 per night (USD)VRBO
Prime Loop Luxury + City & Train Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: 'The Daisy' offers a unique blend of luxury and convenience, perfect for business travelers and tourists. As ...
From $392 per night (USD)VRBO
From $702 per night (USD)Expedia
High-End 3BR Retreat + Steps to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 'The Tulip' offers a luxurious escape near top attractions, hosted by a professional team with a 5-year Superho ...
From $702 per night (USD)Expedia
From $460 per night (USD)VRBO
Prime Lincoln Park Views + Modern Amenities Await
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 'The Elm' is your luxury retreat for the ultimate urban getaway, with scenic views and a location that puts eve ...
From $460 per night (USD)VRBO
From $483 per night (USD)Expedia
Lincoln Park Getaway: Skyline Views & Luxury
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 'The Pine' is the perfect home base for your Chicago adventure. Top dining and city transit are just outside yo ...
From $483 per night (USD)Expedia
From $944 per night (USD)VRBO
Premium 2BR Apartments in Lincoln Park
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: For families and large groups, 'The Ash' makes your Chicago stay easy, offering two spacious apartments with Wh ...
From $944 per night (USD)VRBO
From $526 per night (USD)VRBO
Skyline Views in 3BR Apartment w/ Top Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience top-tier comfort in 'The Frame,' the perfect spacious home base for your travels. Don't just take ...
From $526 per night (USD)VRBO
From $570 per night (USD)VRBO
Modern 2BR in The Loop + Panoramic City Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Looking for a spotless stay in the heart of the action? 'The Violet' delivers, with unmatched city access and a ...
From $570 per night (USD)VRBO
From $1025 per night (USD)VRBO
Event Proximity + Unique Group Retreat in Loop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Discover 'The Lotus,' your group's private sanctuary in the city, with two stylish apartments placing you steps ...
From $1025 per night (USD)VRBO
From $538 per night (USD)VRBO
Top-Floor Oasis: 2BR in Heart of Fulton Market
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to 'The Dada,' where urban sophistication meets art-filled design. Enjoy premier amenities and the top- ...
From $538 per night (USD)VRBO
From $531 per night (USD)Expedia
Chic Fulton Market Oasis + Curated Comfort & Style
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: 'The Boho' offers skyline views and resort-style amenities for tourists seeking a unique Chicago getaway. Boo ...
From $531 per night (USD)Expedia
From $1224 per night (USD)VRBO
Ideal for Groups: Spacious 2BR in The Loop
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Discover 'The Poppy,' your group's vibrant home base in The Loop, offering two stylish apartments with breathta ...
From $1224 per night (USD)VRBO
From $525 per night (USD)Expedia
Stylish 2BR with Skyline Views Near Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to 'The Pine,' your stylish home base in the heart of the Windy City. You can relax in total comfort kn ...
From $525 per night (USD)Expedia
From $1428 per night (USD)VRBO
Downtown Penthouse Huge Patio with Great View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Immerse yourself in comfort with our 3600 sqft unit, featuring a 1400 sqft balcony and stunning city panoramas. This spa ...
From $1428 per night (USD)VRBO
From $1620 per night (USD)VRBO
3 Stylish 2BRs Steps from Magnificent Mile
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
Summary: Designed for a comfortable group getaway, 'The Mary' offers a modern and spacious retreat in the renowned Gold ...
From $1620 per night (USD)VRBO
From $1453 per night (USD)VRBO
3 Central Apartments Ideal for Groups
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
Summary: The ideal solution for your next corporate offsite, 'The Dahlia' offers spacious and sophisticated accommodatio ...
From $1453 per night (USD)VRBO
From $441 per night (USD)Expedia
High-End West Loop 2BR + City Views & Walkability
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Ideal for tourists and business travelers, 'The Terra' boasts a perfect location for city exploration. With 1 ...
From $441 per night (USD)Expedia
From $572 per night (USD)VRBO
Prime 2BR Retreat: Urban Vibes + Views Await
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 'The Lotus' offers an unbeatable downtown experience for urban explorers, complete with remarkable city views a ...
From $572 per night (USD)VRBO
From $1388 per night (USD)VRBO
High-end Luxury Units + Iconic Views for Groups
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: Ideal for groups, 'The Apollo' offers two stylish apartments in a prime location, just steps from Chicago's bes ...
From $1388 per night (USD)VRBO
From $551 per night (USD)VRBO
Two 2BRs Near Millennium Park, Ideal for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Gather your favorite people at 'The Winfrey,' our exclusive offering of two luxury apartments, perfect for your ...
From $551 per night (USD)VRBO
From $1153 per night (USD)VRBO
Gold Coast Group Retreat + Breathtaking Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Discover the perfect group retreat in Chicago's Gold Coast, a collection of two modern 2BR apartments with priv ...
From $1153 per night (USD)VRBO
From $114 per night (USD)VRBO
Amazing River North 1BR w/ Entertainment Area, Pool & Gym, 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 $114 per night (USD)VRBO
From $1001 per night (USD)Expedia
Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Rainbow Guest House. This is a designer owned, fully decorated house located in a perfect Bucktown/Wicker Par ...
From $1001 per night (USD)Expedia
From $435 per night (USD)VRBO
1 Garage Parking/Skyline Rooftop/PingPong/Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Relax in this stunning 2-bedroom, 2-bath condo for up to 8 guests, featuring a king bed, one double bed and one ...
From $435 per night (USD)VRBO
From $406 per night (USD)Expedia
33rd-Floor Penthouse with Breathtaking Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience 'The Harper', a prime 3BR penthouse with panoramic skyline views, perfect for discerning travelers s ...
From $406 per night (USD)Expedia
From $659 per night (USD)VRBO
Dual Penthouse Retreat: Perfect for Groups
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: The premier choice for corporate retreats and family reunions, 'The Adler' offers two stunning penthouses that ...
From $659 per night (USD)VRBO
From $397 per night (USD)Expedia
Spacious & Modern 3BD/2BA Home- Garage Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the heart of Chicago’s lively River West & West Loop, you’re just minutes away from some of Chicago’s best d ...
From $397 per night (USD)Expedia
From $338 per night (USD)VRBO
Urban Oasis in Roscoe Village! Pet friendly and family friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your stylish home away from home in the heart of Roscoe Village, Chicago’s charming “village within the city” ...
From $338 per night (USD)VRBO
From $471 per night (USD)Expedia
Vital Urban: Spa Inspired Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a unique urban spa inspired retreat in Wicker Park, just a 5-minute walk from the Damen Blue Line. Named one ...
From $471 per night (USD)Expedia
From $167 per night (USD)VRBO
Furnished Holiday Gem Lincoln Park Chicago - Red Line/Fullerton L 1 Block
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Chicago's lively Lincoln Park area, you'll find your ideal place to stay. This charming apartment offers ...
From $167 per night (USD)VRBO
From $2661 per night (USD)VRBO
Vacation home just 2 minutes drive to Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, ...
From $2661 per night (USD)VRBO
From $482 per night (USD)VRBO
Near Theaters & Nightlife, Group Fun, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Let 'The Lush' be your group's 4BR home base for exploring the green spaces and excitement of Lincoln Park. Y ...
From $482 per night (USD)VRBO
From $485 per night (USD)Expedia
4BR Steps to \"L\", Explore City, For Groups
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 'The Flux' is your spacious 4BR launchpad to Chicago, located just steps from the 'L' train. It's a proven fa ...
From $485 per night (USD)Expedia
From $487 per night (USD)VRBO
Lincoln Park 4BR, Easy Group Trip, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your friends at 'The Glow,' a modern 4BR in a vibrant, well-connected Chicago neighborhood. Our perfec ...
From $487 per night (USD)VRBO
From $492 per night (USD)Expedia
4BR w/ Free Parking + Easy City Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 'The Aura' is a convenient 4BR retreat in Goose Island, perfect for family or friend getaways. Our 92% 5-star ...
From $492 per night (USD)Expedia
From $479 per night (USD)VRBO
4BR, Steps to Park & Fun, Family-Ready
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Designed for the perfect family getaway, 'The Nova' provides a 4BR home base with easy access to Lincoln Park's ...
From $479 per night (USD)VRBO
From $1520 per night (USD)Expedia
PH w/ Bean & Lake Views, An Elite Stay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The ...
From $1520 per night (USD)Expedia
From $4468 per night (USD)VRBO
Iconic Downtown Penthouses Getaway + City Views
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
Summary: 'The Lyra' pairs two exquisite penthouses for a unique Chicago experience perfect for groups seeking both leisu ...
From $4468 per night (USD)VRBO
From $512 per night (USD)Expedia
Blueground | River North 2bd apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished two bedroo ...
From $512 per night (USD)Expedia
From $234 per night (USD)VRBO
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Looking for a spot during some Cubs games or a concert? Or just a lovely relaxing spot for a weekend in the city? YOU F ...
From $234 per night (USD)VRBO
From $255 per night (USD)Expedia
Charming 3-bedroom apartment with AC and WiFi in marvelous Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chicago is waiting for you at this 3-bedroom apartment. Each bedroom features a comfortable queen bed, perfect for a ple ...
From $255 per night (USD)Expedia
From $1167 per night (USD)VRBO
Retro Disco Cowboy Fun, Walk to Wrigley, Restaurants/Bars! 15 mins to downtown!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to the ultimate Disco Cowboy getaway! This huge house is perfect for bach parties and friends/family trips! Loc ...
From $1167 per night (USD)VRBO
From $238 per night (USD)VRBO
Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $238 per night (USD)VRBO
Burnham King - Staypineapple Chicago Charm & Afternoon Delights in The Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $410 per night (USD)VRBO
Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units
- 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 $410 per night (USD)VRBO
From $410 per night (USD)VRBO
2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park
- 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 $410 per night (USD)VRBO
From $197 per night (USD)VRBO
Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)VRBO
From $197 per night (USD)VRBO
Cozy Room w/ Historic Charm & Modern Amenities in Heart of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)VRBO
From $208 per night (USD)VRBO
Elegant Room w/ Modern Conveniences & Walkable to Major Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)VRBO
From $208 per night (USD)VRBO
Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)VRBO
From $92 per night (USD)VRBO
Cozy, Natural Albany Park Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come relax in this warm, spacious vintage apartment in friendly, livable Albany Park. Owners live upstairs; we are dedic ...
From $92 per night (USD)VRBO
From $185 per night (USD)VRBO
Professionally Managed 1 Bedroom in the Chicago Loop by the Theater District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago, enjoy what this 1-bedroom apartment has to offer. This superb space features a welcoming queen bed, ...
From $185 per night (USD)VRBO
From $398 per night (USD)Expedia
Chicago West Town Row House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Located in Chicago’s West Town neighborhood, you, your family and friends will be close to everything when you stay at t ...
From $398 per night (USD)Expedia
From $104 per night (USD)VRBO
Blueground | River North, balcony & pool, nr Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...
From $104 per night (USD)VRBO
From $439 per night (USD)VRBO
3 Tranquil Eco-friendly Rooms, Fitness Center, Near River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $439 per night (USD)VRBO