Cook Area Rentals
From $383 per night (USD)VRBO
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
New condo in the heart of Chicago Chinatown with 3 bedrooms, 2 baths, a spacious living area and FREE private parking. T ...
From $383 per night (USD)VRBO
From $1264 per night (USD)VRBO
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 20
Luxurious Upscale Duplex Penthouse Property - Sleeps up to 14 people with over 5600 sq ft in this Duplex Penthouse! Rec ...
From $1264 per night (USD)VRBO
From $256 per night (USD)VRBO
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nicely renovated, modern kitchen and bath, comfortable beds, and solar-powered. Great location in a safe neighborhood, J ...
From $256 per night (USD)VRBO
From $614 per night (USD)Expedia
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
This is THE place to stay for all things Chicago. Everything you need is here: * Fabulous well stocked chef's kitch ...
From $614 per night (USD)Expedia
From $148 per night (USD)VRBO
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...
From $148 per night (USD)VRBO
From $253 per night (USD)VRBO
New&Modern Apartment only 4 miles away from Midway Airport.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located 4 miles away from Midway Airport in Chicago, SeatGeek Stadium 4 miles away, 20min to Down Town, and 15min to Amp ...
From $253 per night (USD)VRBO
From $828 per night (USD)VRBO
Luxéry Stay \"Hollywood\" Downtown/McCormick/WinTrust Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience the best of Chicago from this stunning 3-bedroom apartment in the South Loop. With its elegant desig ...
From $828 per night (USD)VRBO
From $285 per night (USD)Expedia
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $285 per night (USD)Expedia
From $639 per night (USD)VRBO
Adorable single family home in Logan Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
I bought this house in Spring of 2016 and have been remodeling and updating it. There are 2 bedrooms upstairs with a ful ...
From $639 per night (USD)VRBO
From $276 per night (USD)Expedia
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and club ...
From $276 per night (USD)Expedia
From $642 per night (USD)VRBO
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Wrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown ...
From $642 per night (USD)VRBO
From $313 per night (USD)VRBO
Best Lincoln Square Location - Spacious 2 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming apartment in an updated 1800s beautiful brick building. Located in the heart of Chicago's Lincoln Square neighb ...
From $313 per night (USD)VRBO
From $454 per night (USD)VRBO
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful, modern and newly furnished 4br/2 bath condo at a desirable location for business conventions and vacation tra ...
From $454 per night (USD)VRBO
From $249 per night (USD)Expedia
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living roo ...
From $249 per night (USD)Expedia
From $224 per night (USD)VRBO
Spacious 2-BR Condo + Free On-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $224 per night (USD)VRBO
From $444 per night (USD)Expedia
Luxury Modern home minutes from Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Newly rehabbed single family home with parking in Chicago's popular Pilsen neighborhood. Close to transportation, 18th s ...
From $444 per night (USD)Expedia
From $483 per night (USD)VRBO
Stylish Corner 2 Bedroom in the Heart of Chicago | 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 $483 per night (USD)VRBO
From $477 per night (USD)VRBO
Fabulous Corner 2 Bedroom 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 $477 per night (USD)VRBO
From $130 per night (USD)VRBO
Luxe West Loop 1BR w/ Gym, Pool, Coworking, walk to UIC, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop with views over the city. It’ll be easy to si ...
From $130 per night (USD)VRBO
From $585 per night (USD)Expedia
Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
In desirable LOGAN SQUARE - 10 minutes from Downtown Chicago, steps away from the new Restaurant Row on Diversey Avenue! ...
From $585 per night (USD)Expedia
From $158 per night (USD)VRBO
Gorgeous Loop 1BR w/ Gym, Pool, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $158 per night (USD)VRBO
From $127 per night (USD)Expedia
Mod West Loop 1BR w/ Pool, Gym, nr. Fulton Market & L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop with views over the city. It’ll be easy to si ...
From $127 per night (USD)Expedia
From $269 per night (USD)VRBO
Generous River North 3BR w/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI324)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the best of Chicago, with this three bedroom apartment in River North with balcony views over the city. It’ll b ...
From $269 per night (USD)VRBO
From $458 per night (USD)Expedia
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Newly remodeled apartment with 4 bedrooms, 4 bathrooms, a spacious & modern living area, FREE private parking and plenty ...
From $458 per night (USD)Expedia
From $447 per night (USD)VRBO
4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 11
Beautiful, modern and newly furnished 4 br/1.5 bath condo at a desirable location for both business conventions and vaca ...
From $447 per night (USD)VRBO
From $224 per night (USD)Expedia
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Charming Oasis! Step into this delightful 3-BR, 1-BA retreat in a friendly neighborhood with views of a ...
From $224 per night (USD)Expedia
From $189 per night (USD)VRBO
Cozy, Comfortable and Convenient apartment. Close to everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully designed space. Very relaxing layout with all the amenities of home. Minutes from Oak Park Arts district. A ...
From $189 per night (USD)VRBO
From $244 per night (USD)Expedia
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $244 per night (USD)Expedia
From $855 per night (USD)VRBO
River North 3BR/2BA: HUGE, Parking, Center Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, re ...
From $855 per night (USD)VRBO
From $954 per night (USD)VRBO
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $954 per night (USD)VRBO
From $139 per night (USD)VRBO
Don't miss out on this one! No cleaning fee.\nIdeal for McCormick Cntr and U of C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Beautiful, comfortable, PRIVATE garden unit of a 3 floor home located in the historic Bronzeville neighborhood of Chicag ...
From $139 per night (USD)VRBO
From $346 per night (USD)VRBO
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city ...
From $346 per night (USD)VRBO
From $905 per night (USD)VRBO
\"Holy Cow\"! 4bed 4bath Duplex Penthouse w/ 3,000 sqft Private Roof-Deck!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
"Wow" Step outside & be face-to-face with the iconic Wrigley Field, home of the Chicago Cubs!! Best Space in Wrigley! ...
From $905 per night (USD)VRBO
From $162 per night (USD)Expedia
Comfort/Clean! Free Parking 15 min ORD/Downtown2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A friendly welcome to all Business travelers & Tourists! Great 1 bed-apartment /kitchen/dining area/living room (queen ...
From $162 per night (USD)Expedia
From $361 per night (USD)VRBO
LakeHouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Entertain in style, practice yoga, or enjoy a glass of wine on this huge private space. Ideal for Corporate Short or Lon ...
From $361 per night (USD)VRBO
From $275 per night (USD)Expedia
Trendy|Comfortable|1BR|Lincoln Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $275 per night (USD)Expedia
From $596 per night (USD)VRBO
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 17
Summary: Our home is a brand-new construction single family residence. Construction was complete in the summer of 2021. ...
From $596 per night (USD)VRBO
From $223 per night (USD)Expedia
3BR Spacious Home Away From Home. Coziest neighborhood in Chicago.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Windy City and home of amazing restaurants, great sports teams, and of course the lake! Whether you are t ...
From $223 per night (USD)Expedia
From $242 per night (USD)VRBO
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautifully decorated second floor apartment has it all. Sunny, spacious and clean. Three large bedrooms with newly ...
From $242 per night (USD)VRBO
From $577 per night (USD)VRBO
Smart Home in Logan Square by the 606 Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This property is a smart home with 3 bedrooms and 2 1/2 bathrooms, with a garage for a small to medium size SUV, which c ...
From $577 per night (USD)VRBO
From $331 per night (USD)VRBO
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $331 per night (USD)VRBO
From $262 per night (USD)Expedia
Charming|Comfortable|1BR|Lincoln Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $262 per night (USD)Expedia
From $288 per night (USD)VRBO
Modern|Aesthetic|2BR|Evanston|Next to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...
From $288 per night (USD)VRBO
From $762 per night (USD)Expedia
Wrigley Field/Lakeview -Entire Home- Large Groups!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 20
"Welcome to your exclusive 2-story haven flooded with natural light! Dual TV areas with brand new 70" and 55" TVs create ...
From $762 per night (USD)Expedia
From $664 per night (USD)VRBO
Million Dollar Views! Luxury Downtown Skyhouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning, Floor to Ceiling Panoramic Skyline Views from this Spacious 3-Bedroom, 2.5 Bath Apartment in the Sky! Located ...
From $664 per night (USD)VRBO
From $212 per night (USD)Expedia
Suite 1 on Southport 4 Queen Beds!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $212 per night (USD)Expedia
From $462 per night (USD)VRBO
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 2,500 square foot brick-and-timber luxury penthouse with 15 foot ceilings located in the heart of the ...
From $462 per night (USD)VRBO
From $364 per night (USD)Expedia
Cubs Playoffs getaway 2BR 2BA Apartment near Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your getaway location in the heart of the Roscoe Village neighborhood of Chicago! A short walk to Wrigley Fie ...
From $364 per night (USD)Expedia
From $383 per night (USD)VRBO
Berwyn FHS Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Updated home, with 2 car garage parking, and public parking. The home was renovated in 2019, so it has updated carpet & ...
From $383 per night (USD)VRBO
From $499 per night (USD)VRBO
Des Plaines FHS Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary - 1400 SF renovated unit is 11 min away from O'Hare Airport! This property has 3 bedrooms, & 2 bathrooms. Master ...
From $499 per night (USD)VRBO
From $140 per night (USD)VRBO
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
The space is two bedrooms with a common area and bathroom. The common area has a sofa (that can be used if there are mor ...
From $140 per night (USD)VRBO
From $599 per night (USD)VRBO
Modern 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $599 per night (USD)VRBO
From $536 per night (USD)VRBO
Extended Stay Elgin FHS Rental - Greenridge Dr
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Updated home, with 2 car garage parking, driveway, and public parking. The home was renovated in 2018, so it presents a ...
From $536 per night (USD)VRBO
From $755 per night (USD)Expedia
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
2400 sf 4-story home in Chicago's East Village. 5 baths, spacious living rooms, fireplace, en-suite spa bath, 2 terraces ...
From $755 per night (USD)Expedia
From $284 per night (USD)VRBO
Palos Hills FHS Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Updated home, with 2 car garage parking, driveway and street parking. The home has updated flooring throughout, and a ki ...
From $284 per night (USD)VRBO
From $1001 per night (USD)Expedia
Only Urban Beach House in Chicago
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Chicago’s ONLY Urban Beach House combines the best of beach life and urban life! Perfect for couples, students, faculty, ...
From $1001 per night (USD)Expedia
From $242 per night (USD)VRBO
Smart Loop 1BR w/ Gym, Pool, W/D, 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 $242 per night (USD)VRBO
From $202 per night (USD)Expedia
Premium Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Gold Coast furnished one bedroom ap ...
From $202 per night (USD)Expedia
From $784 per night (USD)VRBO
Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! Completely REFRESHED w ...
From $784 per night (USD)VRBO
From $486 per night (USD)Expedia
Wrigley Oasis! Steps from the Field! - 3DR/1BA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
***COVID-19 RESTRICTIONS: Due to COVID-19 Restrictions by the City of Chicago, no more than 6 guests can be on the premi ...
From $486 per night (USD)Expedia
From $296 per night (USD)VRBO
LUX CONDO NEAR DOWNTOWN and now offering car rental service.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The whole group will enjoy easy access to everything from this centrally located place. Three stylish bedrooms with priv ...
From $296 per night (USD)VRBO
From $532 per night (USD)VRBO
Stunning 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $532 per night (USD)VRBO
From $211 per night (USD)VRBO
Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Called one of the 12 coolest neighborhoods in the world! - Forbes Magazine 2018-Pilsen- Google it for yourself!! Wake up ...
From $211 per night (USD)VRBO
From $245 per night (USD)Expedia
Walk to Wrigley Field/Monthly Discounts Available
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
My place is close to Wrigley Field, the Metro, Smart Bar, Uncommon Ground, Lakeview, Wrigleyville. You'll love my place ...
From $245 per night (USD)Expedia
From $148 per night (USD)VRBO
A quiet stay while you are away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a gorgeous home in the Frank Loyd Wright historic district in Oak Park, Illinois. You will sleep on a super comf ...
From $148 per night (USD)VRBO
From $269 per night (USD)Expedia
Amazing Gold Coast 2BR w/ Gym & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Rush & Division furnished two bedroom ...
From $269 per night (USD)Expedia
From $280 per night (USD)VRBO
Ideal West Loop 2BR w/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
From $280 per night (USD)VRBO
Click For PricingExpedia
DOWNTOWN STUDIO BY RUSH STREET -GOLD COAST CENTER
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 60
Gold Coast is Downtown Chicago’s best neighborhood to be! This is an “Entire Space” private studio (Hotel size) only for ...
Click For PricingExpedia
From $250 per night (USD)VRBO
Escape to a Private Woodland Estate
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stylish contemporary Chicago area home nestled away from the bustle of city life on a beautiful, peaceful 5 acre forest ...
From $250 per night (USD)VRBO
From $430 per night (USD)Expedia
Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Spectacular Entire Townhome in the hearth of the city! 3 stories and 1900 sq feet of living space for guests with 3 bedr ...
From $430 per night (USD)Expedia
From $430 per night (USD)VRBO
Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Urban Oasis in the hearth of the city enough space for the full Family! Amazing 3 level Spacious Townhome with gated fr ...
From $430 per night (USD)VRBO
From $294 per night (USD)Expedia
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Chicago! Our 3bed/2bath unit is perfect for both leisure & business travelers. We are conveniently located wi ...
From $294 per night (USD)Expedia
From $96 per night (USD)VRBO
Cozy Loop 1BR w/ Deck, Gym, W/D, nr. West Loop & the L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $96 per night (USD)VRBO
From $306 per night (USD)Expedia
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $306 per night (USD)Expedia
From $309 per night (USD)VRBO
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $309 per night (USD)VRBO
From $393 per night (USD)Expedia
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy a Spacious, Homey 3bd Penthouse (+Patio) with your Family & Friends near Grant Park! We are a short walk to Mille ...
From $393 per night (USD)Expedia
From $89 per night (USD)VRBO
Ideal West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, 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 $89 per night (USD)VRBO
From $1481 per night (USD)Expedia
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 21
Time Out magazine calls us one of the Best Chicago Rentals! HUGE mansion with six bedrooms, two living rooms, and four ...
From $1481 per night (USD)Expedia
From $814 per night (USD)VRBO
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Perfectly located in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here ...
From $814 per night (USD)VRBO
From $184 per night (USD)VRBO
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The first floor flat is a large bright 2 bedroom apartment with a new bathroom. The kitchen features Stainless Steel Fag ...
From $184 per night (USD)VRBO
From $536 per night (USD)VRBO
Elgin FHS Rental - Greenridge Dr
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Updated home, with 2 car garage parking, driveway, and public parking. The home was renovated in 2018, so it presents a ...
From $536 per night (USD)VRBO
From $242 per night (USD)VRBO
Summit FHS Rental
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Updated home, with garage and street parking. The home was renovated in 2019, so it presents a modern kitchen ...
From $242 per night (USD)VRBO
From $284 per night (USD)VRBO
✨|Beautiful|Comfy|1br|✨LincolnSq.|Near Wrigley| ✨
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $284 per night (USD)VRBO
From $350 per night (USD)Expedia
✨Rustic Studio Apartment Heart of Lincoln Square✨
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $350 per night (USD)Expedia
From $571 per night (USD)VRBO
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 24
Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home brought to you by ...
From $571 per night (USD)VRBO
From $330 per night (USD)Expedia
Tranquil garden cottage near golf course…
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. There are came ...
From $330 per night (USD)Expedia
From $252 per night (USD)VRBO
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in the heart of Chicago's premier entertainment district • Walk Score 93 (“Walker’s Paradise”) • Free street par ...
From $252 per night (USD)VRBO
From $599 per night (USD)Expedia
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: The Penthouses at Grand Plaza PH#3 This stunning two-story Penthouse soars above Chicago, featuring dramatic li ...
From $599 per night (USD)Expedia
From $347 per night (USD)VRBO
Inviting Stylish Home with Covered Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan mai ...
From $347 per night (USD)VRBO
From $318 per night (USD)Expedia
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $318 per night (USD)Expedia
From $325 per night (USD)VRBO
🌟Homey|Snuggly|Modern|1BR Lakeview - Near Wrigley🌟
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lakeview is home to Wrigleyville, Wrigley field home of the Chicago Cubs and Belmont theatre district which has over 30 ...
From $325 per night (USD)VRBO
From $422 per night (USD)Expedia
Soft Palate & Warm Bricks At A Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $422 per night (USD)Expedia
From $561 per night (USD)VRBO
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lincoln Park is one of the most coveted areas to live or stay in Chicago. DePaul University is less than a block away. L ...
From $561 per night (USD)VRBO
From $228 per night (USD)Expedia
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located right off main bustling streets in Logan Square, i.e. the famous Milwaukee Ave, you definitely won’t need a car ...
From $228 per night (USD)Expedia
From $238 per night (USD)VRBO
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a beautifully remodeled, modern, spacious, and luxuriously furnished 3 bedroom, 2 bath private city apartment. ...
From $238 per night (USD)VRBO
From $311 per night (USD)Expedia
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#5 Experience elevated city living from this stunning penthouse, soaring 52 sto ...
From $311 per night (USD)Expedia
From $313 per night (USD)VRBO
53 Floor MagMile Penthouse Views, Balcony, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Penthouses at Grand Plaza PH#6 This 2-bedroom/2-bath soars 53 floors above Chicago, featuring dramatic livi ...
From $313 per night (USD)VRBO
From $404 per night (USD)Expedia
Historic 1920s Private Bungalow Near Logan Square!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. The only room ...
From $404 per night (USD)Expedia
From $463 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 $463 per night (USD)VRBO
Click For PricingExpedia
Large 12 room house steps to Park, Shopping and Restaurants, 10 minutes to beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Large Jumbo Georgian two story brick house centrally located on the North side of Chicago in a quiet neighborhood with t ...
Click For PricingExpedia