Chicago Rentals
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)Expedia
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)Expedia
From $112 per night (USD)VRBO
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)VRBO
From $382 per night (USD)Expedia
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)Expedia
From $297 per night (USD)VRBO
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)VRBO
From $610 per night (USD)Expedia
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)Expedia
From $531 per night (USD)VRBO
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)VRBO
From $237 per night (USD)Expedia
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)Expedia
From $342 per night (USD)VRBO
Pristine 2BD - 2.5BD Duplex - Chicago - Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover comfort and privacy in our stylish duplex apartment just steps from Lake Michigan. This 2-bedroom, 2.5-bath hom ...
From $342 per night (USD)VRBO
From $613 per night (USD)Expedia
Elegant Historic Duplex in Old Town • Lincoln Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the charm of Chicago’s historic Old Town from this beautiful duplex on a quiet, tree-lined street. Steps to W ...
From $613 per night (USD)Expedia
From $106 per night (USD)VRBO
Cozy 1 bed, furnished apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the beauty of Wrigelyville in this furnished 1-bedroom apartment. Step into a peaceful space where comfort meet ...
From $106 per night (USD)VRBO
From $479 per night (USD)Expedia
Luxury Wrigley Getaway | 2BR + Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the best of Wrigleyville in this stylish 2-bedroom retreat with free parking. Perfect for couples, small fami ...
From $479 per night (USD)Expedia
From $157 per night (USD)VRBO
Vibrant Getaway in the Windy City of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a peaceful stay at this 3-bedroom one bath apartment in Chicago offers the perfect blend of city proximity and res ...
From $157 per night (USD)VRBO
From $334 per night (USD)Expedia
Chicago O’Hare Modern Hotel‑Style Stay w/parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your stylish hotel‑inspired getaway near Chicago’s O’Hare Airport! This bright and spacious 1‑bedroom condo i ...
From $334 per night (USD)Expedia
From $620 per night (USD)VRBO
Wrigley Luxe Stay | 3BR | Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the comfort of our beautifully designed 3-bedroom home just minutes from Wrigley Field! Perfect for families, frie ...
From $620 per night (USD)VRBO
From $426 per night (USD)Expedia
Luxury 4BR Home with Spa Tub & fire place Near UChicago & Obama Center
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, g ...
From $426 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 $531 per night (USD)Expedia
Beautiful Mid-Century Oasis in South Shore.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This mid century masterpiece is one of kind, offering a beautiful open living space with lots of natural light through a ...
From $531 per night (USD)Expedia
From $686 per night (USD)VRBO
3 Units | Near Chicago River | Downtown Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Chicago's River North neighborhood, this hotel offers convenient access to the vibrant dining and nightlife s ...
From $686 per night (USD)VRBO
From $328 per night (USD)Expedia
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Space: Welcome to our beautiful Logan Square apartment! Experience Chicago like a local in this spacious 2-bedroom, ...
From $328 per night (USD)Expedia
From $384 per night (USD)VRBO
Luxury Penthouse Collection PH1 - Fulton Market
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $384 per night (USD)VRBO
From $485 per night (USD)Expedia
Luxury Penthouse Collection PH4 - Fulton Market
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $485 per night (USD)Expedia
From $255 per night (USD)VRBO
Near UChicago, 3BR Apt, Parking, W/D, 2 Workspaces
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Work-ready 3BR, 2BA apartment located just minutes from UChicago and several major hospitals. Once inside, everything is ...
From $255 per night (USD)VRBO
From $243 per night (USD)Expedia
Brown Line Lounge | Curated Moody
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Welcome to Brown Line Lounge. Samantha and I designed this 3BR/2BA North Center apartment around every ...
From $243 per night (USD)Expedia
From $364 per night (USD)VRBO
Modern 3BR Apt Near United Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this brand-new, stylish 3-bed, 2-bath Chicago apartment! Featuring a chic contemporary design with plush velve ...
From $364 per night (USD)VRBO
From $835 per night (USD)Expedia
Spacious 7-bedroom house in gorgeous Lincoln Park Chicago with AC
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 18
Your Chicago adventure begins at this 7-bedroom house. This charming home features a mix of cozy beds, including 4 queen ...
From $835 per night (USD)Expedia
From $172 per night (USD)VRBO
Near Parks & Eats! Elegant Southwest Chicago Home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Quiet Suburban Neighborhood | Ideal for Traveling Medical Professionals Feel at home from day one at this beautifully a ...
From $172 per night (USD)VRBO
From $314 per night (USD)Expedia
Logan Square Boho Getaway - Sleeps 6 - Remodeled
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this cheerful, pet friendly 700 sqft Chicago retreat for 4-6 guests! Newly renovated garden apartment and in a ...
From $314 per night (USD)Expedia
From $3640 per night (USD)VRBO
Sleek New 6BR Greystone - Rooftop, In-Law Ste, Walk to Wrigley & Block to Train
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to your ultimate Chicago getaway. This brand-new, ultra-spacious Greystone sits perfectly at the intersection of ...
From $3640 per night (USD)VRBO
From $144 per night (USD)Expedia
Stylish 2BR Near UChicago – Easy Downtown Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern and stylish 2-bedroom apartment near the University of Chicago. Fully furnished with a stocked kitchen, blackout ...
From $144 per night (USD)Expedia
From $455 per night (USD)VRBO
Cozy 1 Bedroom Apartment 20 Minutes from Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your private Chicago retreat! Conveniently located just 20 minutes from Downtown Chicago and 5 minutes from t ...
From $455 per night (USD)VRBO
From $205 per night (USD)Expedia
2-bedroom apartment in awesome Chicago with cool AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cozy Study — Apartment 1: a private, fully furnished 2 bedroom, 2 bathroom unit in Bronzeville, perfect f ...
From $205 per night (USD)Expedia
From $408 per night (USD)VRBO
Wrigleyville Oasis • Modern Comfort Steps from Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your Wrigleyville Oasis—an inviting, thoughtfully designed apartment perfect for travelers seeking comfort, c ...
From $408 per night (USD)VRBO
From $260 per night (USD)Expedia
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away on a quiet, tree-lined street in Chicago’s Uptown / Sheridan Park, this beautifully renovated 2-bedroom, 1-b ...
From $260 per night (USD)Expedia
From $185 per night (USD)VRBO
Cozy 2BR Near McCormick & Wintrust with Optional Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
When you step inside this bright South Loop suite, the energy of the city fades away. Sunlight fills the space, creating ...
From $185 per night (USD)VRBO
From $311 per night (USD)Expedia
Chicago Gem Near Downtown Steps from La Catedral Café : Family and Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa De Alma Enjoy a comfortable Chicago stay in a convenient neighborhood location with easy access to downt ...
From $311 per night (USD)Expedia
From $113 per night (USD)VRBO
Blueground | Edgewater, gym, nr Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this sophisticated two bedroom Blueground apartment. You’ll love c ...
From $113 per night (USD)VRBO
From $406 per night (USD)Expedia
Lux New Hyde Park Apt by U Chicago, Museum of Science & Industry w/Peloton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Luxury Hyde Park Retreat — Just Steps from History, Culture & UChicago Luxury 3BR/2BA apartment in a fu ...
From $406 per night (USD)Expedia
From $434 per night (USD)VRBO
Relax & Unwind Private, Comfortable, & Convenient
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom apartment is perfect for your escape to Chicago. Featuring three queen beds, it offers a marvelous space ...
From $434 per night (USD)VRBO
From $893 per night (USD)Expedia
The Boho House • Two Private Suites + Parking
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 12
Two private suites. One unforgettable stay. Perfect for groups who want to be together—without sacrificing space. Enjoy ...
From $893 per night (USD)Expedia
From $817 per night (USD)VRBO
Designer 3BR Near Beach & Obama Center
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $817 per night (USD)VRBO
From $808 per night (USD)Expedia
Private Yard Near Beach & Obama Center
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $808 per night (USD)Expedia
From $914 per night (USD)VRBO
The Zen Duplex: Two Private Suites for Groups
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the "Adjoining Suite" life. This dual-level Zen retreat offers the perfect balance for families or groups: st ...
From $914 per night (USD)VRBO
From $1026 per night (USD)Expedia
Designer Home | Steps to the Obama Center & Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $1026 per night (USD)Expedia
From $574 per night (USD)VRBO
Stunning 3bdrm, steps to North Eastern University, Luxurious, Gourmet kitchen🌟
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Greetings from “The Bernard at Hollywood Park” located on the Northside of Chicago! Our luxury three bedroom, one bath a ...
From $574 per night (USD)VRBO
From $115 per night (USD)VRBO
Detached, private, spacious, free garage, fast wifi, 5min to metra in Ravenswood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Fully renovated in July 2025, this charming detached coach house from 1897 blends historic character with modern comfort ...
From $115 per night (USD)VRBO
From $295 per night (USD)VRBO
Chic & Comfy 3-bedroom apartment in Logan Square, family friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our home, situated in a charming residential area of Logan Square, a vibrant neighborhood. Enjoy being walkin ...
From $295 per night (USD)VRBO
From $177 per night (USD)VRBO
Studio Plus at Hilton Grand Vacations Club Chicago Magnificent Mile Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located between Chicago's Magnificent Mile and Navy Pier, Chicago Magnificent Mile, a Hilton Grand Vacations Club, offer ...
From $177 per night (USD)VRBO
From $839 per night (USD)VRBO
Retreat House with Outdoor Hot Tub & Barrel Sauna
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this pleasant house in Chicago. With three bedrooms featuring a king bed, two queen beds, and a pack n play, ...
From $839 per night (USD)VRBO
From $306 per night (USD)VRBO
Pilsen Retreat: 4BR 3BA near Downtown Chicago
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. St ...
From $306 per night (USD)VRBO
From $393 per night (USD)VRBO
Lovely 3-bedroom condo Walking Distance to United Center and Futon for extra bed
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chicago is waiting for you at this 3-bedroom condo. Inside, guests find two full beds and one queen bed, also included a ...
From $393 per night (USD)VRBO
From $308 per night (USD)VRBO
Spacious 3BR near United Center: Deck & Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience ultimate comfort in this charming home, steps away from the United Center. Catch a game or concert, ...
From $308 per night (USD)VRBO
From $606 per night (USD)VRBO
Luxury Penthouse COMBO 07/04 Terrace | River North
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Enjoy the combination of your luxury two-story designer styled apartment located in River North - the city's c ...
From $606 per night (USD)VRBO
From $661 per night (USD)VRBO
Luxury Penthouse COMBO 07/02 Terrace | River North
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Enjoy the combination of your luxury designer styled apartment located in River North - the city's center of n ...
From $661 per night (USD)VRBO
From $154 per night (USD)VRBO
2-bedroom 1 bath stylish apartment in nice Chicago for relaxing stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable apartment is the perfect home base for your trip to Chicago. Guests will enjoy two comfortable bedrooms, ...
From $154 per night (USD)VRBO
From $250 per night (USD)VRBO
Quirky Quarters at Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: I think you are just going to love my apartment. The space features wonderful large street level windows in th ...
From $250 per night (USD)VRBO
From $222 per night (USD)VRBO
The Gilded Grid | Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience modern luxury just moments from Wrigley Field in this brand-new 4-bedroom, 3.5-bath duplex that sleeps up to ...
From $222 per night (USD)VRBO
From $129 per night (USD)VRBO
Peaceful 3-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this marvelous apartment in Chicago. With three comfortable bedrooms and two bathrooms, guests have plenty of ...
From $129 per night (USD)VRBO
From $108 per night (USD)VRBO
Cozy Stay in Chicago/ 2 Bedroom/ Up to 4 People/32+ Days Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for a cozy, convenient place to stay in Chicago? This charming apartment in Roger’s Park is the perfect. This fu ...
From $108 per night (USD)VRBO
From $205 per night (USD)VRBO
Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Chicago is waiting for you! Enjoy our newly remodeled impeccably clean, cozy and peaceful 1-bedroom supreme comfort in t ...
From $205 per night (USD)VRBO
From $330 per night (USD)VRBO
Modern Design 3 BDR Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your stylish retreat in Avondale! This beautifully appointed 3-bedroom apartment seamlessly blends modern luxur ...
From $330 per night (USD)VRBO
From $524 per night (USD)VRBO
Shorter Walk To Wrigley Than A Home Run
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unit is a shorter walk to Wrigley Stadium than a home run. Catty-corner to Wrigley Field, you'll be at the center ...
From $524 per night (USD)VRBO
From $158 per night (USD)VRBO
West Loop Living • New Furniture • Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home in the heart of Chicago's West Loop. This thoughtfully furnished high-rise condo com ...
From $158 per night (USD)VRBO
From $289 per night (USD)VRBO
West Town Gem: 3-Bedroom Spacious Apartment
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your home away from home in Chicago's charming West Town neighborhood. Start your morning with the ...
From $289 per night (USD)VRBO
From $170 per night (USD)VRBO
2-bedroom house on a quiet, tree-lined street with modern amenities throughout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
A Comfortable Chicago Home Base — Pet-Friendly & Work-Ready Welcome to your Chicago home away from home, set in a quiet ...
From $170 per night (USD)VRBO
From $202 per night (USD)VRBO
Stylish 1BR/1BA Near Lake in Rogers Park + Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Rogers Park is Chicago’s northernmost lakefront neighborhood, known for its beaches, parks, and tree-lined streets lined ...
From $202 per night (USD)VRBO
From $418 per night (USD)VRBO
Luxury Living in Bronzeville with Oversized Rooftop.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a peaceful stay at this 3-bedroom building in Chicago. The charming space features three queen beds, offering plen ...
From $418 per night (USD)VRBO
From $860 per night (USD)VRBO
Luxury Gold Coast Duplex -8 Bedrooms 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 15
Summary: Whether you're planning a family reunion, group getaway, corporate retreat, or celebrating a special occasion, ...
From $860 per night (USD)VRBO
From $233 per night (USD)VRBO
West Town Lookout • Spacious • Modern • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a bright, open-concept home where oversized windows flood the space with natural light and high ceilings creat ...
From $233 per night (USD)VRBO
From $897 per night (USD)VRBO
Luxury Oasis in the Heart of the City with Incredible Private Roof Deck & Patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning designer 3 bedroom-3 bathroom home in Chicago's trendy Ukrainian Village—minutes from the Loop & steps to the t ...
From $897 per night (USD)VRBO
From $246 per night (USD)VRBO
Welcome to our 2-Bed Apartment in West Town for 7!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Experience Chicago from the heart of vibrant West Town. Start your morning with coffee in a bright, open livin ...
From $246 per night (USD)VRBO
From $197 per night (USD)VRBO
Cozy 1BR Near Loyola University • Fast WiFi • Walk to Dining & Transit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Settle into this cozy and inviting apartment—perfect for travelers in town for school, work, or a relaxing escape. Ideal ...
From $197 per night (USD)VRBO
From $205 per night (USD)VRBO
2BR/1BA Apt w/ Modern Amenities Rogers Park + Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rogers Park is Chicago’s northernmost lakefront neighborhood, known for its beaches, parks, and tree-lined streets lined ...
From $205 per night (USD)VRBO
From $260 per night (USD)VRBO
Comfy Condo - Gym, Free Parking & Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the best of Chicago's lakefront from this Edgewater retreat, just minutes from the Granville Red Li ...
From $260 per night (USD)VRBO
From $299 per night (USD)VRBO
Modern Furnished 2BR in Pilsen Near Medical District & Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a relaxed, stylish stay in this fully furnished 2-bedroom, 1-bath apartment located in Chicago’s vibrant Pilsen ne ...
From $299 per night (USD)VRBO
From $213 per night (USD)VRBO
Spacious Modern Pilsen Retreat | Sleeps 8 | Near Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your home away from home in the heart of Chicago's vibrant Pilsen neighborhood! Entire apartment id ...
From $213 per night (USD)VRBO
From $403 per night (USD)VRBO
Andi's Treehouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
We open our home to guests during the summer. You will have the whole top floor of this historic 1889 4 story greystone ...
From $403 per night (USD)VRBO
From $207 per night (USD)VRBO
Edgewater Apt with Free Parking, Gym, City Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the charm of Chicago's Edgewater neighborhood, where lakefront mornings and local cafés are just mo ...
From $207 per night (USD)VRBO
From $221 per night (USD)VRBO
Chic 2BR Apartment in Edgewater: Gym & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience the best of Chicago's lakefront from this Edgewater retreat, just minutes from the Granville Red Li ...
From $221 per night (USD)VRBO
From $247 per night (USD)VRBO
Spacious 4-bedroom apartment in gorgeous Chicago with AC and gym
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Discover the beauty of Chicago from this 4-bedroom apartment. The space features a queen bed, a twin bed, and two bunk b ...
From $247 per night (USD)VRBO
From $217 per night (USD)VRBO
Pet-Friendly Uptown Chicago Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
Summary: 2 bedroom Unit in Uptown Chicago The Space: 2 bedroom home with 2 bathrooms that sleeps 11. Bed sizes a ...
From $217 per night (USD)VRBO
From $275 per night (USD)VRBO
Edgewater Glen 3BD Cozy Retreat Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience a delightful stay in this 3BR, 1.5BA home in Edgewater. Start your morning with coffee in the shar ...
From $275 per night (USD)VRBO
From $135 per night (USD)VRBO
Serene 2-bedroom apartment with AC in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bedroom apartment. The adorable space features two queen beds, perfect for a ...
From $135 per night (USD)VRBO
From $307 per night (USD)VRBO
Chic River North Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to your stylish home base in the heart of River North, one of Chicago’s most vibrant and walkable neig ...
From $307 per night (USD)VRBO
From $333 per night (USD)VRBO
All Season Chicago Haven Near United Center Rush Hospital and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this charming apartment in Chicago. With two comfortable bedrooms featuring a king and a queen bed, guests ca ...
From $333 per night (USD)VRBO
From $170 per night (USD)VRBO
Prime 3BR/2BA in the Heart of Chicago. 10 mins to Dine & Downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy a peaceful stay at this 3-bedroom apartment in Chicago. The space features two queen beds and one full bed, provid ...
From $170 per night (USD)VRBO
From $348 per night (USD)VRBO
3BR Retreat Perfect for Professionals and Families in South Shore/ Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your home away from home! This fully renovated 3-bedroom, 2-bathroom apartment offers modern comfort in the h ...
From $348 per night (USD)VRBO
From $348 per night (USD)VRBO
Chic Luxe Spa Retreat - Light Filled+King Bed+Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light fr ...
From $348 per night (USD)VRBO
From $420 per night (USD)VRBO
Patio • Workspace • Dog Friendly • Free Street Parking • Train Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll fall in love with this garden apartment that offers easy access to both the O'Hare airport & the heart of Chicago ...
From $420 per night (USD)VRBO
From $394 per night (USD)VRBO
Sleek Avondale Condo Spa Bath King Bed +Queen bed +Garage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern meets mmm-hmm in this 2BR Avondale gem. King & queen beds? Check. Spa bath with rain shower & jets? Oh yes. Strea ...
From $394 per night (USD)VRBO
From $151 per night (USD)VRBO
Cozy 1-bedroom apartment in beautiful West Loop, in-unit laundry + pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy up in this serene space in one of Chicago's most beautiful neighborhoods, the West Loop. This superb one-bedroom is ...
From $151 per night (USD)VRBO
From $148 per night (USD)VRBO
Feel at Home while Exploring Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay comfortably in Chicago at this 2-bedroom apartment. The space features one queen bed and one twin bed, plus a cozy ...
From $148 per night (USD)VRBO
From $379 per night (USD)VRBO
Spacious West Loop Retreat UnitedCenter & Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bright and spacious top-floor condo in a 2-unit building, on a quiet and safe residential street. Perfect for couples, ...
From $379 per night (USD)VRBO
From $294 per night (USD)VRBO
Peaceful 3-bedroom apartment in charming Chicago Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This 3-bedroom apartment is perfect for your escape to Chicago. Inside, guests find a wonderful mix of comfort with a qu ...
From $294 per night (USD)VRBO
From $186 per night (USD)VRBO
River North / Mag Mile, Lake and City Views, 43rd Floor Condo, Parking Included!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In this breathtaking NE corner apartment at Huron and Wabash, every window frames the mesmerizing Chicago Skyline and La ...
From $186 per night (USD)VRBO
From $282 per night (USD)VRBO
Stay near Wrigley Field! Spacious 3BD Penthouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your spacious Lakeview retreat just steps from Wrigley Field! Catch a Cubs game, explore the neighb ...
From $282 per night (USD)VRBO
From $280 per night (USD)VRBO
Lakeview 3BD 2BA Penthouse near Wrigley Field!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the best of Chicago from this modern 3-bed, 2-bath Lakeview retreat, just steps from Wrigley Field, ...
From $280 per night (USD)VRBO
From $101 per night (USD)VRBO
Cozy 1-bedroom garden apartment in W Lakeview/Wrigley/Roscoe Village/Fast WIFI
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bright 1BR & 1 Bath in Prime Lakeview — great for long stays, remote work, or city trips! What You’ll Love: • Fast WiFi ...
From $101 per night (USD)VRBO