Cook Area, Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Cook Area, Illinois on RentalSaver.com!

Cook Area Rentals

From $433 per night (USD)
VRBO
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
In the heart of Lakeview, still close to downtown, museums and McCormick Place. A quick stroll to Lake Michigan and the ...
From $433 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Urban Luxury Home In Downtown Chicago!
Bedrooms:
3
Bathrooms:
3
Sleeps:
14
Enjoy a stay at a world travelers' custom designed home! **PLEASE READ DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $349 per night (USD)
VRBO
From $595 per night (USD)
VRBO
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Bedrooms:
4
Bathrooms:
4
Sleeps:
18
Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for ...
From $595 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Downtown Guild #4 | Mag Mile, Gold Coast, The Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $237 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy a stay at a world travelers' Windy City home! **PLEASE READ FULL DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $330 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Extended Stay 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 $260 per night (USD)
VRBO
From $483 per night (USD)
VRBO
Magic Factory Loft 2West
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spacious Bright & Spotlessly Clean in the Heart of Everything Chicago - Chef Kitchen 3 bedrooms, 2 full baths Sleeps 8 g ...
From $483 per night (USD)
VRBO
From $87 per night (USD)
VRBO
Modern Coach House 2BR/1BA/Den in Hyde Park/ Kenwood, walk to U of C & Lakefront
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Kenwood Coach House| Rear Coach House Fully Furnished! Near U of C Hospital Hospital Staff/ Clinical Rotations REQUIRE ...
From $87 per night (USD)
VRBO
From $103 per night (USD)
VRBO
Mod Loop 1BR, w/ Gym, Pool nr the Millenium Park by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $103 per night (USD)
VRBO
From $99 per night (USD)
Expedia
Ideal River North 1BR w/pool, gym, nr. L & Magnificent Mile
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 $99 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Hip Loop 1BR w/ Gym, Pool, W/D, nr. Financial District, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $237 per night (USD)
VRBO
From $99 per night (USD)
Expedia
Cozy West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $99 per night (USD)
Expedia
From $138 per night (USD)
VRBO
Hip River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Rush & Division furnished one bedroom ap ...
From $138 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Bright Loop 1BR w/ Gym, Roofdeck, 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 $163 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Extended Stay Elk Grove Village FHS Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
1900 SF unit is 5 min away from O'hare, and 12 min from downtown Schaumburg, which is like a bustling mini Chicago, incl ...
From $240 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Elk Grove Village FHS Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
1900 SF unit is 5 min away from O'hare, and 12 min from downtown Schaumburg, which is like a bustling mini Chicago, incl ...
From $240 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Top floor of Historic Oak Park Home /2 Car Garage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Fran ...
From $304 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, zoo, and Lincoln park, restaurants, ...
From $488 per night (USD)
Expedia
From $631 per night (USD)
VRBO
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
Bedrooms:
2
Bathrooms:
4
Sleeps:
20
Lots of room for you to stretch out and enjoy the great location in East Lakeview. Nearby to public transportation incl ...
From $631 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Extended Stay 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 $430 per night (USD)
VRBO
From $161 per night (USD)
VRBO
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This gorgeous 2bed/2bath packs a powerful punch, and more amenities than you'll know what to do with. -1 Private Parkin ...
From $161 per night (USD)
VRBO
From $772 per night (USD)
VRBO
Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Our unique Lincoln Park Rowhouse is located in the heart of Lincoln Park and is perfect for your next group gathering in ...
From $772 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Quiet, family getaway. Puppers welcome!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This aparrtment is the top floor of a two flat. It's located in a very quiet, family friendly neighborhood. The skylight ...
From $245 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $181 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Beautiful Streeterville 1BR w/ Deck & Pool, walk to Beach, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Streeterville furnished one bedroom apa ...
From $233 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Trendy 2BR Apartment in Logan Square!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Whatever brings you to town, our bright and airy two-bedroom apartment unit is complete with everything you need to feel ...
From $207 per night (USD)
VRBO
From $1234 per night (USD)
VRBO
Entire house 1 city block from Wrigley Field.
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
We are very excited to prepare this amazing 2 story (with basement) home for your future stays. We are located in the he ...
From $1234 per night (USD)
VRBO
$Chicago's Hidden Treasure \Evanston, IL\ Urban Luxury with comfort$
From $275 per night (USD)
Expedia
Chicago's Hidden Treasure \"Evanston, IL\" Urban Luxury with comfort
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $275 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Half a mile from everything in the heart of Evanston, Illinois
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $275 per night (USD)
VRBO
From $127 per night (USD)
VRBO
Bright and Cozy 1BR Apartment in Logan Square!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our 1-bedroom/1 bath apartment is perfect for getaway to Chicago. We're located in the trendy Logan Square neighborhood. ...
From $127 per night (USD)
VRBO
From $842 per night (USD)
VRBO
Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
🛏 Sleeping Arrangements, Plenty of room for everyone to have their own space! Bedroom 1: King bed Bedroom 2: Queen bed ...
From $842 per night (USD)
VRBO
From $92 per night (USD)
Expedia
Luxe West Loop Studio 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. It’ll be easy to simply show up and start li ...
From $92 per night (USD)
Expedia
From $315 per night (USD)
VRBO
❤️ Spacious and Airy Apartment With Parking On Site!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $315 per night (USD)
VRBO
From $99 per night (USD)
Expedia
Gorgeous Loop 1BR w/ Pool, Gym, nr. Financial District by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one bedroom ...
From $99 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Spacious Loop 1BR w/ Pool, Gym, nr. the L & Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished one bedroom a ...
From $173 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Woodlawn Oasis...10 Minutes to Dining & Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $467 per night (USD)
Expedia
From $308 per night (USD)
VRBO
The NICEST place in Evanston for Families 1500Main
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
No Additional Cleaning Fee! --- Fully Furnished 2-story, 2 bedroom attached Townhouse/Duplex with a new King bed in th ...
From $308 per night (USD)
VRBO
From $193 per night (USD)
Expedia
The Avondale Guesthouse
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $193 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Stunning Logan Square 2BR w/ Roof Deck & Gym, 1 block to L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Logan Square with balcony views over the city. It’ll be ...
From $200 per night (USD)
VRBO
From $380 per night (USD)
Expedia
NEW LUXURY PENTHOUSE CONDO
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $380 per night (USD)
Expedia
From $328 per night (USD)
VRBO
The Country Life - house
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
The Country life is a beautiful suburban home just 20 minute from Chicago. The entire house is yours to take in this pea ...
From $328 per night (USD)
VRBO
From $1109 per night (USD)
VRBO
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
Bedrooms:
6
Bathrooms:
6
Sleeps:
28
Walk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars ...
From $1109 per night (USD)
VRBO
From $388 per night (USD)
VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city an ...
From $388 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Spectacular Corner 3BR in the Loop | City Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $522 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Warm and Cheerful 3 Bedroom Winnetka Townhouse
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Stay in comfort in the ChicagoLand north shore in a 3 bedroom, 1.5 bath, 2-car garage townhome only blocks from Metra ra ...
From $407 per night (USD)
VRBO
From $242 per night (USD)
VRBO
Extended Stay 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 $2796 per night (USD)
VRBO
The Orleans - Entire Building - With Rooftop Deck!
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $2796 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Mid Century Elegance in Evanston Vintage Apartment.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Evanston and a short walk from Evanston's Central Street Business District, and scenic Lake Michigan beaches, ...
From $319 per night (USD)
VRBO
From $214 per night (USD)
VRBO
LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streetervil ...
From $214 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $192 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Airy West Loop 1BR w/ Pool, Pet Spa, near Restaurant Row, 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 $210 per night (USD)
VRBO
From $1313 per night (USD)
VRBO
6 Bedrooms Home Suburbs of Chicago
Bedrooms:
5
Bathrooms:
6
Sleeps:
20
This is an incredible home designed to accommodate the traveler seeking a memorable family escape to modern/contemporary ...
From $1313 per night (USD)
VRBO
From $169 per night (USD)
VRBO
Sunny Evanston 2BR, 1 mile from Northwestern campus, by Blueground
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Evanston with this sophisticated two bedroom Blueground apartment. You’ll love ...
From $169 per night (USD)
VRBO
From $133 per night (USD)
Expedia
Modern Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Logan Square furnished one bedroom apar ...
From $133 per night (USD)
Expedia
From $676 per night (USD)
VRBO
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Bedrooms:
3
Bathrooms:
5
Sleeps:
22
Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost eve ...
From $676 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Cozy Loop 1BR w/ Pool, Gym, nr. Merchandise Mart & L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $167 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Retro Apartment in Andersonville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full o ...
From $159 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Modern Wrigley Oasis with Parking!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Beautifully designed in the heart of Wrigley. Steps away from Wrigley Field, bars, restaurants and shops! This modern oa ...
From $297 per night (USD)
Expedia
From $2624 per night (USD)
VRBO
Modern Victorian With Old World Charm
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This historic Queen Anne home built in 1889 is in the heart of Oak Park, just a few minutes walk to Frank Lloyd Wright h ...
From $2624 per night (USD)
VRBO
From $1486 per night (USD)
VRBO
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME!!! ABSOLUTELY NO PARTIES OR LARGE GATHERINGS! We reserve the right t ask ...
From $1486 per night (USD)
VRBO
$Chicago's Hidden Treasure, \EVANSTON, IL\$
From $275 per night (USD)
VRBO
Chicago's Hidden Treasure, \"EVANSTON, IL\"
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $275 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Fun / Bright / Cubs Apt | Near Wrigley!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: A short 10 minute walk from Wrigley Field (0.8 miles) , and everything the popular Wrigleyville has to offer. ...
From $168 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Sleek West Loop 1BR w/ Gym, Pool, near Fulton Market, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $208 per night (USD)
VRBO
From $96 per night (USD)
Expedia
Premium Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable Logan Square furnished one bedroo ...
From $96 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Lincolnwood FHS Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2000 SF renovated unit is 20 minutes away from O’hare Airport & 18 min to downtown Chicago! This property has 3 bedrooms ...
From $536 per night (USD)
VRBO
From $536 per night (USD)
VRBO
Extended Stay Lincolnwood FHS Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2000 SF renovated unit is 20 minutes away from O’hare Airport & 18 min to downtown Chicago! This property has 3 bedrooms ...
From $536 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Extended Stay Hoffman Estates FHS Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1400 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O’hare Air & downtown! This prope ...
From $238 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Hoffman Estates FHS Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1400 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O’hare Air & downtown! This prope ...
From $237 per night (USD)
VRBO
From $297 per night (USD)
VRBO
A home away from home! <No events allowed>
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
vacation rental cleaning protocol Major surfaces are sanitized and disinfected. Major surfaces include countertops, ...
From $297 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Upgraded,Spacious 3 Bedroom Apartment.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Bright and beautiful top floor 1200 sq. ft, 3 bedrooms apartment located in Jefferson Park,9 minutes from O hare Interna ...
From $296 per night (USD)
VRBO
From $80 per night (USD)
VRBO
Thirty Day Minimum Condo in Chicago SW Suburbs of Orland Park Illinois
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Remodeled first floor condo walking distance to Orland Mall, grocery stores, and restaurants and great for a traveling n ...
From $80 per night (USD)
VRBO
From $304 per night (USD)
Expedia
NEW LUXURY CONDO WITH PATIO DECK
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $304 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfec ...
From $567 per night (USD)
VRBO
Click For Pricing
Expedia
Hip West Loop 2BR w/ Gym, Pool, near Fulton Market, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
Click For Pricing
Expedia
From $140 per night (USD)
VRBO
Mod West Loop 2BR w/ Gym, Pool, W/D, nr. Fulton Market, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
From $140 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Mod River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Rush & Division with high floor views over the city. It ...
From $167 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Near North with views over the city. It’ll be easy to s ...
From $105 per night (USD)
VRBO
From $114 per night (USD)
Expedia
Open River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with high floor views over the city. It ...
From $114 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Roomy River North 2BR w/ Gym, Deck & Pool, walk to Mag Mile, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Rush & Division furnished two bedroom ...
From $169 per night (USD)
VRBO
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Expedia
Smart West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one bedroom ...
Click For Pricing
Expedia
From $211 per night (USD)
VRBO
Ideal Gold Coast 2BR, w/ Gym, Lounge, W/D, nr Oak Street by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $211 per night (USD)
VRBO
From $836 per night (USD)
Expedia
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Welcome to an amazing, 3-story art filled modern single family home in Chicago's vibrant RiverWest neighborhood. 3500 s ...
From $836 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Gorgeous Home Near Wrigley Field
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Modern design of a historic Chicago row house in one of the "cities best" neighborhoods. This home was totally redesigne ...
From $457 per night (USD)
VRBO
From $1491 per night (USD)
Expedia
Nice cozy home to experience on your vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Nice 3 bedroom 2 bathroom with laundry room. Nice walkthrough garage. The house is amazing with hardwood floors and kitc ...
From $1491 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Updated Forest Park 3 BR Bungalow
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This charming and recently updated 3BR bungalow in a friendly neighborhood is perfect for families, business travelers, ...
From $202 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Flossmoor FHS Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
2200 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 4 bedrooms ...
From $300 per night (USD)
VRBO
From $219 per night (USD)
VRBO
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy comfort and casual elegance in your own house in a quiet Evanston Neighborhood. Located on Chicago's North Shore ...
From $219 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Extended Stay Flossmoor FHS Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
2200 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 4 bedrooms ...
From $303 per night (USD)
VRBO
From $675 per night (USD)
VRBO
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Live like a local in one of Chicago’s best neighborhoods! Located in a family-owned boutique building in the vibrant and ...
From $675 per night (USD)
VRBO
From $344 per night (USD)
Expedia
BEAUTIFUL 4/20 FRIENDLY 2 BR 2 BA DUPLEX -TWO FLOORS - IN SIZZLING SOUTH SHORE!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We invite you to our beautiful home, minutes from Downtown, Hyde Park, Golfing, Fishing, and the Beach! Floor 1 feature ...
From $344 per night (USD)
Expedia
From $617 per night (USD)
VRBO
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
20
Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen an ...
From $617 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Trendy West Town Flat - 2 bed / 1.5 bath with parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Find your wanderlust in this perfectly located West Town condo. Situated between Chicago’s West Loop and Wicker Park ne ...
From $315 per night (USD)
Expedia
From $569 per night (USD)
VRBO
The Greenleaf House—Whole House
Bedrooms:
2
Bathrooms:
7
Sleeps:
12
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gat ...
From $569 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Beautiful 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 $446 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
*Please inquire before requesting to book* 4 bedroom 2 bath apartment. In the Historic up and coming kenwood neighbor ...
From $371 per night (USD)
VRBO
$\Serenity of Evanston\ 2 BDR/2Bath Modern-Luxe Suite$
From $345 per night (USD)
Expedia
\"Serenity of Evanston\" 2 BDR/2Bath Modern-Luxe Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Modern-Luxe experience at the Serenity of Evanston Condo. Elegant finishes. Resort-like amenities with fitness center, o ...
From $345 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Unique Apt. in Upscale Evanston with Easy Access to Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Southwest comes to the Windy City. Relax and enjoy your stay on Chicago's North Shore in our charming vintage Casita. L ...
From $218 per night (USD)
VRBO
Click For Pricing
Expedia
“The Estates Suite” PRIVATE BEDROOM in our Home and use of the Hottub.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
PRIVATE ROOM IN OUR HOME AS WE LIVE IN THE PROPERTY. NOT ENTIRE HOUSE!!! The “Estates Suite” is an affordable place wi ...
Click For Pricing
Expedia
From $397 per night (USD)
VRBO
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Summary: Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of ...
From $397 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Luxury, spacious first floor brownstone in east Lincoln Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the best of Chicago’s neighborhoods, parks and lakefront from the comfort of this 2400 square foot home with two s ...
From $376 per night (USD)
VRBO

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