Chicago Rentals
From $355 per night (USD)VRBO
Luxury Penthouse Loft w/Terrace 507 | River North
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: BRAND NEW PENTHOUSE DUPLEX LOFT IN THE HEART OF RIVER NORTH WITH PRIVATE TERRACE! Enjoy your luxury two-sto ...
From $355 per night (USD)VRBO
From $307 per night (USD)Expedia
Luxury Penthouse Loft w/Terrace 504 | River North
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: BRAND NEWPENTHOUSE DUPLEX LOFT IN THE HEART OF RIVER NORTH WITH PRIVATE TERRACE! Enjoy your luxury two-sto ...
From $307 per night (USD)Expedia
From $366 per night (USD)VRBO
Luxury Designer Loft 202 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $366 per night (USD)VRBO
From $355 per night (USD)Expedia
Luxury Designer Loft 302 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $355 per night (USD)Expedia
From $355 per night (USD)VRBO
Luxury Designer Loft 402 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: BRAND NEW LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chicago's cen ...
From $355 per night (USD)VRBO
From $355 per night (USD)Expedia
Luxury Designer Penthouse Loft 502 | River North
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW PENTHOUSE LOFT IN THE HEART OF RIVER NORTH! Enjoy your luxury designer styled loft located in Chi ...
From $355 per night (USD)Expedia
From $262 per night (USD)VRBO
Luxury 3BR Suite with Patio & Skyline Views, Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious 3-Bedroom Suite with Private Patio & Skyline Views Your elevated Chicago experience starts here. Wake up to ...
From $262 per night (USD)VRBO
From $311 per night (USD)Expedia
3-bedroom apartment in lovely Chicago with AC and comfort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Nestled in Chicago, this wonderful ground unit apartment offers a comfortable stay for guests seeking a home away from h ...
From $311 per night (USD)Expedia
From $126 per night (USD)VRBO
Peaceful 1-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the beauty of Chicago from this 1-bedroom apartment. Guests enjoy a peaceful living room with a queen bed, perf ...
From $126 per night (USD)VRBO
From $295 per night (USD)Expedia
Chicago 2BR 27th Floor Skyline Views - 5 Min walk Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wake up in this modern Chicago suite designed for modern urban living in the heart of downtown. Elevated high above the ...
From $295 per night (USD)Expedia
From $306 per night (USD)VRBO
Corporate apartment with 2 bedrooms and fantastic view of lake and skyline
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Located in Chicago, this corporate apartment is a cool retreat for travelers. With two bedrooms, including one cozy quee ...
From $306 per night (USD)VRBO
From $104 per night (USD)Expedia
Private Room Healthcare Pros Welcome 15 Min to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 6
- Sleeps:
- 2
Clean, comfortable private room in Chicago's Bridgeport neighborhood — just 15 minutes from the Medical District and Do ...
From $104 per night (USD)Expedia
From $234 per night (USD)VRBO
Bright 2BR Retreat near McCormick & Museum Campus
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wake up to Chicago’s glittering skyline from your private 2BR, 2BA suite right on iconic Michigan Avenue. Sip your morni ...
From $234 per night (USD)VRBO
From $235 per night (USD)Expedia
Hyde Park University of Chicago Penthouse 3 bedroom/2 bathroom + gym & office
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chicago is waiting for you at this 3-bedroom apartment. Each bedroom features a king bed, offering guests a tremendous a ...
From $235 per night (USD)Expedia
From $87 per night (USD)VRBO
The Jewels, 2 bed/2 bath, UChicago 2mi, Parking, DTWN 15mi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its resi ...
From $87 per night (USD)VRBO
From $974 per night (USD)Expedia
Near Zoo and Beach • Reading Nook + Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the best of Chicago from this newly renovated 3-bedroom apartment in the heart of Lincoln Park. Just minutes ...
From $974 per night (USD)Expedia
From $594 per night (USD)VRBO
Discover the Heart of Chicago from Our Modern 3 Bed/ 2.5 Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to a stylish stay in this modern, charming, family-friendly home just minutes from picturesque downtown Chicago. ...
From $594 per night (USD)VRBO
From $258 per night (USD)Expedia
Spacious 3BR Suite with Skyline Views Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome and Experience the best of Chicago in this modern, high-rise 3-bedroom, 2-bathroom suite — located in the vibran ...
From $258 per night (USD)Expedia
From $474 per night (USD)VRBO
West Loop Condo w/Parking + Gym - Walk to Fulton Market
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your Chicago home base in one of the city’s most sought-after neighborhoods. This stylish condo blends comfor ...
From $474 per night (USD)VRBO
From $453 per night (USD)Expedia
Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our new townhome offering in Chinatown. This 3-story home has 4 queen beds to accommodate 8+ guests. An outdo ...
From $453 per night (USD)Expedia
From $199 per night (USD)VRBO
Modern 2BR/2BA Corner Suite Near McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your modern 2-bedroom, 2-bathroom corner suite offers unbeatable convenience and comfort, located just steps ...
From $199 per night (USD)VRBO
From $276 per night (USD)Expedia
Nice 4-bedroom apartment near everything
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
Discover this 4-bedroom apartment in Chicago. The space features a king bed, two queen beds, and a full bed, comfortably ...
From $276 per night (USD)Expedia
From $482 per night (USD)VRBO
23PL - 4 Bedroom/2 Bath - Chinatown, McCormick Place
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our humble home. A beautiful two levels that combined to offer 4+ bedrooms, 2 baths, 2 living rooms, 2 dining ...
From $482 per night (USD)VRBO
From $465 per night (USD)Expedia
Boho City Escape | Parking + Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a Boho City Escape designed for comfort, style, and easy Chicago living. This bright 2-bed, 2-bath stay features c ...
From $465 per night (USD)Expedia
From $409 per night (USD)VRBO
Modern Zen Retreat mins from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this modern boho retreat in the heart of Ukrainian Village. Thoughtfully designed with botanical accents, natu ...
From $409 per night (USD)VRBO
From $276 per night (USD)Expedia
2 bedroom 1.5 in Boystown a short walk to Wrigley Field, close to everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience Chicago like a local in this 2-bedroom apartment. One room has a queen bed with a small offshoot room with a ...
From $276 per night (USD)Expedia
From $346 per night (USD)VRBO
Spacious & Renovated 3BR/2BA Full Kitchen. Steps from McCormick Place & the Loop
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your spacious, sun-drenched, freshly renovated retreat in a quiet, family-friendly Chicago neighborhood. Bri ...
From $346 per night (USD)VRBO
From $118 per night (USD)VRBO
Blueground | Fulton River District, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Fulton River District furnished one ...
From $118 per night (USD)VRBO
From $110 per night (USD)VRBO
Blueground | Fulton River District, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Fulton River District furnished one be ...
From $110 per night (USD)VRBO
From $191 per night (USD)Expedia
Modern 2BR Suite w/ Skyline View Near McCormick Place & Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your elevated stay in the heart of Chicago’s vibrant South Loop! This bright and modern 2-BR, 2-BA suite is l ...
From $191 per night (USD)Expedia
From $475 per night (USD)VRBO
Charming 3-bedroom bungalow 15 min south of Chicago ,15 min from Obama Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago, enjoy what this 3-bedroom bungalow has to offer. This amazing space features two bathrooms and keeps ...
From $475 per night (USD)VRBO
From $1019 per night (USD)Expedia
Premier 5BR Art Deco duplex with garage.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to the Wrigleyville Art Deco Executive Duplex, a spacious 5-bedroom, two-story retreat designed for memorable gr ...
From $1019 per night (USD)Expedia
From $2001 per night (USD)VRBO
Premier 9BR Art Deco manor with garage.
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 22
Welcome to The Addison Art Deco Manor Estate, a 4,200 sq ft private 9-bedroom residence just steps from Wrigley Field. D ...
From $2001 per night (USD)VRBO
From $196 per night (USD)Expedia
Charming Cozy Compact Studio- free street Parking- McCormick-Chinatown-RateField
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Compact Studio Near McCormick, Chinatown & Sox Stadium This 1st-floor compact studio (approx. 200–250 sq. ft.) offers a ...
From $196 per night (USD)Expedia
From $233 per night (USD)VRBO
4-bedroom apartment in fabulous Chicago with AC for your stay
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
This memorable apartment is the perfect home base for your trip to Chicago. With four comfortable bedrooms featuring two ...
From $233 per night (USD)VRBO
From $513 per night (USD)Expedia
4BR Retreat w/ Theater, Arcade, Gym and Firepit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Mobile Chicago 934 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Not ...
From $513 per night (USD)Expedia
From $622 per night (USD)VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Saint Paul Chicago 293 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...
From $622 per night (USD)VRBO
From $401 per night (USD)Expedia
Private Gym and Workspace • 3BR in Quiet Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to Osage Chicago 461 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $401 per night (USD)Expedia
From $511 per night (USD)VRBO
Stylish 3BR Apt | Gym and Workspace | Near O’Hare
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Osage Chicago 805 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $511 per night (USD)VRBO
From $191 per night (USD)Expedia
Pilsen Gem Near the Loop and Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in our cozy private one-bedroom coach house with a comfy living room, sofa bed, kitchenette, and full bathroom. Ups ...
From $191 per night (USD)Expedia
From $804 per night (USD)VRBO
Grand 5,500 sq ft Pilsen home, 5BR, sleeps 11, near downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Luxe 5BR Pilsen Home, Chef's Kitchen, Sleeps 11 One of Pilsen's most striking homes. Four floors of open space with 12- ...
From $804 per night (USD)VRBO
From $663 per night (USD)Expedia
Spacious 3BR 2BA Haven City Views Steps to MagMile
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Welcome to The Haven — a sunlit 3BR retreat in the heart of The Loop with skyline views and steps-from-the-par ...
From $663 per night (USD)Expedia
From $1539 per night (USD)VRBO
Luxury PH: Panoramic Views + Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Temporary housing doesn't have to feel temporary. The Sol, a 4-bedroom penthouse on the 23rd floor in the Chic ...
From $1539 per night (USD)VRBO
From $218 per night (USD)Expedia
✨ Beautiful 2BR Apartment with Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and unwind in this stylish and comfortable 2-bedroom apartment in Chicago, thoughtfully designed to offer the perf ...
From $218 per night (USD)Expedia
From $305 per night (USD)VRBO
Location Jackpot! Minutes to Downtown, McCormick & Chinatown-free parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
## Location Jackpot! Minutes to Downtown, McCormick Place & Chinatown Looking for the perfect blend of city excitement a ...
From $305 per night (USD)VRBO
From $274 per night (USD)Expedia
Historic Family Home | Walk to U Chicago, Obama Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a refined bohemian retreat just steps from the University of Chicago and one mile from the Obama Presidential Ce ...
From $274 per night (USD)Expedia
From $596 per night (USD)VRBO
Fabulous 3-bedroom townhome with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready to relax in this 3-bedroom townhome in Chicago. The space features one king bed and two queen beds, perfect fo ...
From $596 per night (USD)VRBO
From $626 per night (USD)Expedia
Gold Coast Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the heart of Chicago, where River North meets the storied Gold Coast, one of the city’s most walkable neighborho ...
From $626 per night (USD)Expedia
From $212 per night (USD)VRBO
Modern 1BR Near Midway - CTA Train - Golf Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Skip the cramped hotel room. This spacious, modern 1-bedroom near Chicago Midway Airport gives you the room to breathe, ...
From $212 per night (USD)VRBO
From $295 per night (USD)Expedia
Skyline 24th Floor Near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $295 per night (USD)Expedia
From $705 per night (USD)VRBO
Envitae Hotel, 4BR Modern Sleek Apartment
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed fo ...
From $705 per night (USD)VRBO
From $359 per night (USD)Expedia
Skyline Luxury 19th Floor Retreat Near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $359 per night (USD)Expedia
From $295 per night (USD)VRBO
Luxury 21st floor Skyline Views near Grant Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $295 per night (USD)VRBO
From $1228 per night (USD)Expedia
McCormick Meetup - Prime Location - Sleeps 16
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Spacious Chicago Retreat for Large Groups, Business Travel & Extended Stays Welcome to your home away from home in Ch ...
From $1228 per night (USD)Expedia
From $272 per night (USD)VRBO
Modern 1BR w/ Workspace near O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 563 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $272 per night (USD)VRBO
From $365 per night (USD)Expedia
1BR Near O'Hare • Balcony • Workspace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 506 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...
From $365 per night (USD)Expedia
From $295 per night (USD)VRBO
18th floor 2BR Grant Park Suite with Balcony, Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Stay in a luxury 2-bedroom, 2-bath high-rise suite in downtown Chicago near Grant Park, Millennium Park, and the Lakefro ...
From $295 per night (USD)VRBO
From $355 per night (USD)Expedia
Newgard Nest I Walk to Loyola, Beaches & CTA l Bright 2nd FL Apt w/ Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful 2nd-floor, 3-bedroom apartment in Rogers Park near Loyola University and the lake. Ideal for families, visiting ...
From $355 per night (USD)Expedia
From $795 per night (USD)VRBO
Spacious 3-bedroom apartment in lovely Chicago with FREE Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. This delightful space features three comfortable bedrooms and a well-ap ...
From $795 per night (USD)VRBO
From $496 per night (USD)Expedia
Luxury 4br duplex Lakefront Living Without the Downtown Price
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this adorable apartment in picturesque Chicago. With four cozy bedrooms—three featuring queen beds and one wit ...
From $496 per night (USD)Expedia
From $125 per night (USD)VRBO
2-bedroom walkable 2 BLOCKS University of Chicago & President Obama Center Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to this FULLY FURNISHED charming condo in Woodlawn. Walking distance to LAKEFRONT, New President Obama Library C ...
From $125 per night (USD)VRBO
From $344 per night (USD)Expedia
5 Minutes to Wrigley + Sauna + Games + Free Garage Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cute 700 sqft ground floor unit 2BR 2BA In the heart of beautiful and fun Lakeview, minutes from Wrigleyville and Montro ...
From $344 per night (USD)Expedia
From $568 per night (USD)VRBO
Modern& Spacious 2BR with Garage Parking in Chicago's Prime Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago, this marvelous apartment offers guests a comfortable retreat with two cozy bedrooms and a well-appoi ...
From $568 per night (USD)VRBO
From $578 per night (USD)Expedia
Spacious 1BR apartment in welcoming Chicago with Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this 1-bedroom apartment in Chicago. The space offers a peaceful retreat with cozy heating and air ...
From $578 per night (USD)Expedia
From $891 per night (USD)VRBO
Logan Sq 4BR Duplex • Garage • Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perched on the entire third floor of a classic Chicago brick building, this private 4-bedroom, 2-bath duplex gives your ...
From $891 per night (USD)VRBO
From $224 per night (USD)Expedia
Stylish Midway Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Chicago home! This comfortable 2-bedroom retreat is perfect for families, couples, business travelers, or ...
From $224 per night (USD)Expedia
From $68 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North Side furnished studio apa ...
From $68 per night (USD)VRBO
From $150 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $150 per night (USD)Expedia
From $89 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Near North Side furnished studio apart ...
From $89 per night (USD)VRBO
From $75 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Near North Side. It’ll be easy to simply show up and start l ...
From $75 per night (USD)VRBO
From $156 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Near North Side furnished one bedroom ap ...
From $156 per night (USD)VRBO
From $98 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North Side furnished one bedroo ...
From $98 per night (USD)Expedia
From $154 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Tribune Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $154 per night (USD)VRBO
From $155 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Chicago River
- 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 $155 per night (USD)Expedia
From $98 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Chicago River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty studio Blueground apartment. You’ll love coming home t ...
From $98 per night (USD)VRBO
From $172 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Near North Side. It’ll be easy to simply show up and st ...
From $172 per night (USD)Expedia
From $73 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Near North Side furnished studio apart ...
From $73 per night (USD)VRBO
From $77 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Near North Side furnished one bedroom ...
From $77 per night (USD)Expedia
From $151 per night (USD)VRBO
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North Side furnished two b ...
From $151 per night (USD)VRBO
From $149 per night (USD)Expedia
Blueground | Near North Side, rooftop, nr Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...
From $149 per night (USD)Expedia
From $621 per night (USD)VRBO
Modern& Spacious 2BR in Prime Location with 1 Parking Spot
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home in the heart of Chicago's iconic Lincoln Park neighborhood! This beautifully appointed 1-bedroom ap ...
From $621 per night (USD)VRBO
From $474 per night (USD)Expedia
2 br, 2 bt, UChicago Coachman's Guesthouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChic ...
From $474 per night (USD)Expedia
From $232 per night (USD)VRBO
Vibrant, walkable Andersonville Gem-easy access to Wrigley, venues and Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this apartment in picturesque Chicago. With 3 comfortable bedrooms featuring 2 queen beds and 1 king bed, gues ...
From $232 per night (USD)VRBO
From $1112 per night (USD)Expedia
The Beverly Hills of Chicago Luxury Stay
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your luxury home away from home in the "Beverly Hills of Chicago." Thoughtfully designed for families, friend ...
From $1112 per night (USD)Expedia
From $348 per night (USD)VRBO
Luxury King Bed • Remodeled Safe Chicago Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to River Chicago 362 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ✨ What ...
From $348 per night (USD)VRBO
From $284 per night (USD)Expedia
Chicago Haven simple comfort with a touch of style
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Chicago Haven blends modern comfort with a welcoming, home-like atmosphere-ideal for solo travelers, professionals and f ...
From $284 per night (USD)Expedia
From $986 per night (USD)VRBO
Gold Coast Pristine 5BR - 3.5BA - Patio - Parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Free Garage Parking!! Experience the best of Chicago in this stunning multi-level Gold Coast residence. Perfect for gro ...
From $986 per night (USD)VRBO
From $394 per night (USD)Expedia
Stylish 5BR West Loop Retreat with Optional Parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Experience comfortable city living in this home near Downtown Chicago. Featuring hardwood floors, stainless steel applia ...
From $394 per night (USD)Expedia
From $131 per night (USD)VRBO
Affordable and Convenient Room with King-Size Bed – Ideal for Relaxing Stays
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $131 per night (USD)VRBO
From $131 per night (USD)VRBO
Plan Your Stay in a Peaceful Room w/ King Bed Near Midway International Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $131 per night (USD)VRBO
From $144 per night (USD)VRBO
Affordable Stay Near Midway Airport – King-Size Comfort + Convenient Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $144 per night (USD)VRBO
From $144 per night (USD)VRBO
Budget-Friendly King Room Perfect for a Relaxing Getaway near Soldier Field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our rooms offer comfort and convenience with plush beds, free Wi-Fi, flat-screen TVs, and private bathrooms. Just 1.8 mi ...
From $144 per night (USD)VRBO
From $129 per night (USD)VRBO
Entire Apartment Next to Wrigley Field.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious 2-Bedroom Apartment Steps from Wrigley Field Enjoy the best of Chicago from this stylish and spacious 2-bedroo ...
From $129 per night (USD)VRBO
From $112 per night (USD)Expedia
Warm Modern 2BR • Walkable Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A calm, furnished 2BR in a classic 1912 two-flat in Roscoe Village. Original stained glass, built-ins, wood floors, dini ...
From $112 per night (USD)Expedia
From $382 per night (USD)VRBO
Calling all Cubs Fans: Beautiful 4-bedroom condo across from Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This 4-bedroom condo is perfect for your escape to Wrigleyville in Chicago. The lovely space features a king bed, two qu ...
From $382 per night (USD)VRBO
From $297 per night (USD)Expedia
Dreamy South Loop Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your cloud-like escape in Chicago's South Loop. This bright, spacious retreat is designed for comfort, featur ...
From $297 per night (USD)Expedia
From $610 per night (USD)VRBO
Spacious 4-bedroom townhome in fantastic Bronzeville Chicago Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Stay in this beautiful 4BR, 3.5BA greystone in historic Bronzeville—just a few doors from the former home of Bo Diddley, ...
From $610 per night (USD)VRBO
From $531 per night (USD)Expedia
Spacious 5-bedroom house in Chicago with AC Near Obama Center & UChicago
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your spacious Chicago home away from home! This beautifully furnished 5-bedroom, 2.5-bath home is perfect for ...
From $531 per night (USD)Expedia
From $237 per night (USD)VRBO
The Nook • Vintage Flat Near Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $237 per night (USD)VRBO
From $382 per night (USD)Expedia
One-of-a-Kind Apartment In Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This unique and spacious two bedroom garden unit is the perfect place for anyone visiting Chicago! You won't r ...
From $382 per night (USD)Expedia