Cook Area Rentals
From $128 per night (USD)VRBO
Deluxe West Loop 1BR w/ Rooftop, Gym & Grills, nr Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cheery Near West Side furnished one bedroom a ...
From $128 per night (USD)VRBO
From $106 per night (USD)VRBO
Delightful 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 Near West Side. It’ll be easy to simply show up and sta ...
From $106 per night (USD)VRBO
From $246 per night (USD)VRBO
Cozy 2 Bedroom unit-15mins Dwtn!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...
From $246 per night (USD)VRBO
From $287 per night (USD)Expedia
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $287 per night (USD)Expedia
From $186 per night (USD)VRBO
McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...
From $186 per night (USD)VRBO
From $294 per night (USD)Expedia
Spacious 3BR Suite South Loop Chicago Near McCormick Place & Soldier Field
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your stylish and spacious 3-bedroom, 2-bathroom urban getaway in the heart of Chicago’s South Loop! Perfectly ...
From $294 per night (USD)Expedia
From $653 per night (USD)VRBO
Modern, Luxe, House 20mins to Downtown, Private Rooftop, 2car Garage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $653 per night (USD)VRBO
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 $103 per night (USD)VRBO
Dreamy West Loop 1BR w/ Rooftop & Dog Wash, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near West Side. It’ll be easy to simply show up and sta ...
From $103 per night (USD)VRBO
From $346 per night (USD)Expedia
Bee's Knees - Ritzy, 1924 Chicago Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bee's Knees - a vintage gem with a Hollywood-glam twist! This 4-BR Chicago bungalow home is the perfect getaw ...
From $346 per night (USD)Expedia
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 $322 per night (USD)Expedia
3B Spacious Home+ Free Parking near Chicago O'Hare
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
It is a lovely spacious and cozy home (recently updated) with FREE PARKING nestled in a peaceful neighborhood in the Chi ...
From $322 per night (USD)Expedia
From $386 per night (USD)VRBO
Beautiful Suburban Home 30 minutes from downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Alone, with friends, or with family? Whatever your needs, this house is sure to fulfill your expectations. Full house in ...
From $386 per night (USD)VRBO
From $529 per night (USD)VRBO
Modern Bungalow near the beach! 20 minutes to downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
This stylish home is perfect for group trips. With only 26 minutes to Midway airport and less than 10 minutes to the nea ...
From $529 per night (USD)VRBO
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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 ...
Click For PricingVRBO
From $301 per night (USD)Expedia
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home features 4 bedrooms, 2 full baths, a living room, and a fully stocked kitchen that you can cook your own delic ...
From $301 per night (USD)Expedia
From $134 per night (USD)VRBO
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 $134 per night (USD)VRBO
From $575 per night (USD)Expedia
Haus Of Hues: MDRN Bright Peaceful Private Apt
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Peaceful and centrally-located, this flat is the perfect place to relax with the whole family or explore the city with f ...
From $575 per night (USD)Expedia
From $1032 per night (USD)VRBO
8 Bedrooms, 3 Full Bathrooms, 2 Kitchens and 2 Parking Spaces
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 10
This House was built in 1902 and was modified into 2 apartments in the 1940's. The house has 3 levels and many stairs. I ...
From $1032 per night (USD)VRBO
From $540 per night (USD)Expedia
Balcony, Gym, 1 Garage Parking, Tempur-Pedic Bed!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 3-bedroom West Loop apartment with Gym access, Private Balcony & Reserved Garage Parking. Sleeps 12 g ...
From $540 per night (USD)Expedia
From $273 per night (USD)VRBO
Designer Apartment 10 Min Walk to Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Stunning 2 bedroom apartment with 1 King bed and 1 Queen bed. You are a 5 min walk to Wrigley Field, Home o ...
From $273 per night (USD)VRBO
From $432 per night (USD)Expedia
Designer Apt, Billiards, Private Patio, 1 Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Stunning 3 bedroom modern garden unit apartment with 1 Gated Parking Space, Pool Table (Also a dining table), ...
From $432 per night (USD)Expedia
From $394 per night (USD)VRBO
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Remodeled 2BR Retreat | Steps to the El (Brown line) & Minutes to Wrigley Experience the best of Chicago’s vibrant Nort ...
From $394 per night (USD)VRBO
From $462 per night (USD)Expedia
Modern Apt, Billiards, 1 Private Patio,1 Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Stunning 3-bedroom modern garden unit with gated parking, a pool table that doubles as a dining table, and a p ...
From $462 per night (USD)Expedia
From $384 per night (USD)VRBO
House in the Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Bring the whole family to this great place with lots of room across the street for fun fishing, golfing, bike track, val ...
From $384 per night (USD)VRBO
From $476 per night (USD)Expedia
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Evanston, enjoy what this 4-bedroom house has to offer. With 4 queen beds, our property provides ample space ...
From $476 per night (USD)Expedia
From $195 per night (USD)VRBO
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a peaceful stay at this 1-bedroom apartment in Hickory Hills. This serene and quaint property offers everything yo ...
From $195 per night (USD)VRBO
From $386 per night (USD)VRBO
4-bedroom townhome in Frank Lloyd Wright District-FREE PARKING, Patio, Yard
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
After a long day of enjoying all that Chicago (our place is just a short walk to the green line which gets you in the he ...
From $386 per night (USD)VRBO
From $496 per night (USD)VRBO
Cozy apartment near zoo, DePaul, Oz Park and much more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $496 per night (USD)VRBO
From $403 per night (USD)Expedia
Chic & Spacious Bi-Level Bucktown Condo - Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This one-of-a-kind condo in Bucktown is ready to host! The property features a hidden staircase leading down to the in-l ...
From $403 per night (USD)Expedia
From $252 per night (USD)VRBO
3br with Private Entrance - Garden Unit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our private 3 bedroom garden condo in trendy Logan Square. This urban retreat offers a cozy living space with ...
From $252 per night (USD)VRBO
From $223 per night (USD)Expedia
The Landmark; a comfy suite near McCormick Place
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the landmark. A cozy well appointed studio space in the heart of the historic Calumet/Giles Prairie district ...
From $223 per night (USD)Expedia
From $413 per night (USD)VRBO
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 18
Gorgeous gem within 10 miles of Downtown, Airport, Lake Michigan, and United Center! About 15 miles from Wrigley Field ...
From $413 per night (USD)VRBO
From $403 per night (USD)VRBO
Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this fabulous 3-bedroom gem in Chicago. This wonderful house offers a cozy and inviting atmosphere that will ma ...
From $403 per night (USD)VRBO
From $260 per night (USD)VRBO
Spacious 4-bedroom apartment with AC and WiFi in terrific Chicago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 14
Stay comfortably in Chicago at this 4-bedroom apartment. Marvelous and superb, this amazing property offers 4 queen beds ...
From $260 per night (USD)VRBO
From $245 per night (USD)Expedia
Cozy 1-bedroom house in charming Chicago Free Easy Parking , AC, Washer & Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unwind in Chicago at this lovely newly renovated home! Nestled in the heart of West Town, this amazing property offers a ...
From $245 per night (USD)Expedia
From $397 per night (USD)VRBO
5 Star Luxury Stay Near Chicago O'hare Airport, King Beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Chicago O'Hare Airport is just 10 minutes away. Enjoy a stylish stay with your whole family at this luxurious 5-star pro ...
From $397 per night (USD)VRBO
From $980 per night (USD)Expedia
2-Story 4-Bedroom Condo: 3-minute walk to Wrigley Field. King Bed
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Just one block from Wrigley Field! Includes air hockey, ping-pong, foosball, and oversized Connect 4 in the basement ga ...
From $980 per night (USD)Expedia
From $362 per night (USD)VRBO
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers ever ...
From $362 per night (USD)VRBO
From $167 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 $167 per night (USD)Expedia
From $244 per night (USD)VRBO
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
A spacious updated bungalow at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Nei ...
From $244 per night (USD)VRBO
From $311 per night (USD)Expedia
Sacramento - Stylish 2BR Apt in Irving Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
<p>Welcome to our charming basement unit in the heart of Irving Park! This inviting space is perfect for small families, ...
From $311 per night (USD)Expedia
From $295 per night (USD)VRBO
Walk to Lake Michigan: Chicago Apt w/ Yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Peaceful Surroundings | Relax on the Deck | < 1 Mi to 0.6 miles to Oakwood Beach Experience the magic of the Windy Cit ...
From $295 per night (USD)VRBO
From $503 per night (USD)Expedia
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bed, 2-bath condo. The space offers a lovely living room with a sofa that can ...
From $503 per night (USD)Expedia
From $344 per night (USD)VRBO
‘Cozi Crib23’ 4 Mi to Obama Center, Soldier Field
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet Neighborhood Coffee Bar | Easy Hwy Access | 11 Mi to Dtwn Experience the best of the Windy City at this family-fr ...
From $344 per night (USD)VRBO
From $233 per night (USD)Expedia
Charming Pilsen Studio - Quick Access to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the charm of our unique studio apartment in La Vecindad, your perfect retreat in Pilsen, Chicago! This cozy stu ...
From $233 per night (USD)Expedia
From $459 per night (USD)VRBO
The Haven near Downtown, Medical District and United Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are traveling to Chicago for a special event at the united center or visiting a loved one at one of Chicago's pre ...
From $459 per night (USD)VRBO
From $223 per night (USD)Expedia
Beautiful 3-Bedroom Apartment, Free WiFi & AC, 18 Minutes to Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Make this spacious and memorable 3-bedroom apartment your home away from home while visiting Chicago! Designed for famil ...
From $223 per night (USD)Expedia
From $281 per night (USD)VRBO
Game Room, Deck & Yard: Chicago Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Retreat to The Windy City and book this 2-bedroom, 3.5-bath Chicago vacation rental! This abode features an updated inte ...
From $281 per night (USD)VRBO
From $265 per night (USD)Expedia
Chic Euro City Getaway- Close to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated 3 bedroom/ 1.5 bath apartment is the perfect home for exploring Chicago! The closest metro station ...
From $265 per night (USD)Expedia
From $444 per night (USD)VRBO
Spacious 4-bedroom house in charming Des Plaines with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Comfort and Fun at our house in Des Plaines, IL Single family wrench in quiet neighborhood. Houses up to 8 p ...
From $444 per night (USD)VRBO
From $173 per night (USD)Expedia
1-bedroom condo next to Chicago Midway International Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Your Chicago adventure begins at this delightful 1-bedroom condo. The cozy bedroom features a queen bed, while the bathr ...
From $173 per night (USD)Expedia
From $238 per night (USD)VRBO
Chic 1-bedroom apartment in phenomenal Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the beauty of Chicago from this enchanting 1-bedroom apartment. With a cozy living room featuring a futon, gues ...
From $238 per night (USD)VRBO
From $431 per night (USD)VRBO
Windy City Getaway | 3BR 2BA Chicago Townhouse by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience Chicago up close and personal when you stay at this 3-bedroom, 2.5-bathroom vacation rental. Boasting stylis ...
From $431 per night (USD)VRBO
From $445 per night (USD)VRBO
Charming 1-bedroom apartment with AC, WiFi in phenomenal Park Ridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This memorable apartment is the perfect home base for your trip to Park Ridge. With a cozy bedroom, AC, heating, WiFi, a ...
From $445 per night (USD)VRBO
From $320 per night (USD)Expedia
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 a ...
From $320 per night (USD)Expedia
From $1266 per night (USD)VRBO
Downtown Penthouse 5bd VIEWS | Parking, Gym
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Two 2-Story Downtown Penthouses (Combined Units) with M ...
From $1266 per night (USD)VRBO
From $593 per night (USD)Expedia
Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chic + spacious w/A+ location! 2024 gut-rehab. One of two apartments a two-flat. This unit = Main floor + finished bsmnt ...
From $593 per night (USD)Expedia
From $301 per night (USD)VRBO
The Burrow at Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Expect to find a relatively dark and moody interior filled with interesting things. The location is exceptiona ...
From $301 per night (USD)VRBO
From $465 per night (USD)Expedia
Pine Beam Sloth Apartment next to Blue Line
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our charming 650 sq ft, 1-bedroom apartment! It`s the perfect size for comfortable living, offering a well-e ...
From $465 per night (USD)Expedia
From $320 per night (USD)VRBO
The Green House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Freshly fabulous is this completely renovated home with all new furnishings. Set in the heart of Schaumburg and central ...
From $320 per night (USD)VRBO
From $1053 per night (USD)Expedia
2 Connecting Suites at a 4.5⭐️ Hotel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
1 King Bed and 1 Double Sofa Bed500-sq-foot room with city views Layout - Bedroom and sitting areaInternet - Free WiFi 2 ...
From $1053 per night (USD)Expedia
From $1674 per night (USD)VRBO
2 Connecting Suites at a 4⭐️ Hotel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1 King Bed800-sq-foot room with river views Layout - Dining area and sitting areaInternet - WiFi 50+ Mbps Entertainment ...
From $1674 per night (USD)VRBO
From $605 per night (USD)Expedia
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
NEW HOME/NEWLY FURNISHED! This 6 bed single family home is ready to host! My space accomodates 12 guests with 6 beds and ...
From $605 per night (USD)Expedia
From $112 per night (USD)VRBO
Chic 2-bedroom apartment in fabulous Chicago with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Chicago adventure begins at this 2-bedroom apartment. The space features two bedrooms and a third bedroom used as a ...
From $112 per night (USD)VRBO
From $498 per night (USD)Expedia
\"Melody of Evanston\" 3BD, 2BA UrbanLux Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your Evanston adventure begins at this charming 3-bedroom condo. With a king bed, queen bed, dual twin beds, and a dorm ...
From $498 per night (USD)Expedia
From $793 per night (USD)VRBO
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 $793 per night (USD)VRBO
From $486 per night (USD)Expedia
Spacious 3br home near Chicago, fenced yard for pets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Modern Family Home in Quiet Neighborhood - Close to Chicago Welcome to our spacious 2800 sqft single-family home, perfe ...
From $486 per night (USD)Expedia
From $239 per night (USD)VRBO
Entire home, close to highway, serene neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your family will enjoy easy access to Northbrook, Wilmette, and Chicagoland from this conveniently located home that is ...
From $239 per night (USD)VRBO
From $1159 per night (USD)Expedia
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1159 per night (USD)Expedia
From $577 per night (USD)VRBO
Discover Downtown from Our Well-Appointed Space | 2 Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $577 per night (USD)VRBO
From $274 per night (USD)Expedia
3-bedroom apt .on North Side! Great location between downtown and the airport.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Discover this 3-bedroom gem in Chicago. Remodeled basement unit apartment in the Belmont Cragin neighborhood. Central No ...
From $274 per night (USD)Expedia
From $741 per night (USD)VRBO
Exquisite Chicago Modern Rooftop, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to our chic retreat in Dunning, Chicago. This modern unit sleeps 9 comfortably in 3 spacious bedrooms and 2 lux ...
From $741 per night (USD)VRBO
From $270 per night (USD)VRBO
The Suite Spot • Eclectic • Modern • 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 $270 per night (USD)VRBO
From $657 per night (USD)VRBO
Dream Stay - Modern Bungalow Near Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful bungalow in Home Sweet Homewood with upscale decor and finishes. Stay comfortably in this 4-bedroom house. Wit ...
From $657 per night (USD)VRBO
From $395 per night (USD)Expedia
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious 1200 sqft 3BR 1BA located 10-15 min from Downtown! Tub/Shower Games for adults & kids 5 Smart TVs, free fast wi ...
From $395 per night (USD)Expedia
From $437 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 ev ...
From $437 per night (USD)VRBO
From $438 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 y ...
From $438 per night (USD)Expedia
From $665 per night (USD)VRBO
Prime 4BR Penthouse w/ Skyline Views for Families
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Your family's perfect Chicago retreat awaits at 'The Soul,' a spacious 4BR penthouse featuring a kids' room, t ...
From $665 per night (USD)VRBO
From $577 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 ta ...
From $577 per night (USD)VRBO
From $430 per night (USD)VRBO
Sky-High 2BR w/ Gym & City Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Discover ultimate relaxation at 'The Avant,' perfect for tourists seeking a vibrant stay in Fulton Market. ...
From $430 per night (USD)VRBO
From $483 per night (USD)Expedia
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 ...
From $483 per night (USD)Expedia
From $430 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 $430 per night (USD)VRBO
From $430 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. ...
From $430 per night (USD)Expedia
From $483 per night (USD)VRBO
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 k ...
From $483 per night (USD)VRBO
From $1744 per night (USD)Expedia
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 $1744 per night (USD)Expedia
From $304 per night (USD)VRBO
Downtown 2bd #4 - Near Grant Park, Museums, Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $304 per night (USD)VRBO
From $938 per night (USD)VRBO
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 $938 per night (USD)VRBO
From $1185 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 $1185 per night (USD)VRBO
From $358 per night (USD)Expedia
4 bedrooms, 6 beds, 2 full baths, and open basement loft
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
4 bedrooms, 6 beds, 2 full baths, and open basement loft. Your family of 10+ persons will be close to everything when yo ...
From $358 per night (USD)Expedia
From $2611 per night (USD)VRBO
Sleek New 4BR Greystone - Rooftop, Walk to Wrigley & 1 Block to Brown Line Train
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your ultimate Chicago getaway. This brand-new, ultra-spacious Greystone sits perfectly at the intersection of ...
From $2611 per night (USD)VRBO
From $213 per night (USD)Expedia
Peloton available in the APT, WiFi, access to very fun restaurants and bars
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to this fantastic apartment in Chicago. This cozy space offers one bathrooms equipped with a shower, bathtub, an ...
From $213 per night (USD)Expedia
From $174 per night (USD)VRBO
Spacious 4-bedroom house in fabulous Chicago Back Yard Pond, and Theatre
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Chicago is waiting for you at this 4-bedroom house. With 2 queen beds, 1 bunk bed, and 1 twin bed, this lovely property ...
From $174 per night (USD)VRBO
From $540 per night (USD)Expedia
Historic Manor House Private Guest Suite Evanston
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the Guest Suite of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches ...
From $540 per night (USD)Expedia
From $1674 per night (USD)VRBO
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 $1674 per night (USD)VRBO
From $180 per night (USD)VRBO
Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in comfort in this 1-bedroom 2nd floor apartment located in Historic village of Oak Park. Impeccably restored, the ...
From $180 per night (USD)VRBO
From $795 per night (USD)VRBO
Spacious 3-bedroom corporate condo in wonderful North Kenwood in Hyde Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Your Chicago adventure begins at this 3-bedroom corporate apartment. With 3 queen beds, 1 king bed, and 1 full bed, this ...
From $795 per night (USD)VRBO
From $246 per night (USD)VRBO
Jumbo 3bd In Hot Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Bring the whole family to this great place with lots of room for fun Comfortable 1100 sqft 3 BR 1 BA located in the beau ...
From $246 per night (USD)VRBO
From $457 per night (USD)VRBO
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 $457 per night (USD)VRBO
From $318 per night (USD)Expedia
Charming Home in Portage Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This cozy four-bedroom, two-bathroom home is ideally located near O’Hare Airport and downtown Chicago, offering convenie ...
From $318 per night (USD)Expedia