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

Chicago Rentals

From $338 per night (USD)
VRBO
Urban Oasis in Roscoe Village! Pet friendly and family friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your stylish home away from home in the heart of Roscoe Village, Chicago’s charming “village within the city” ...
From $338 per night (USD)
VRBO
$Spacious 3BR Apartment with Patio & BBQ, Minutes from Downtown & CTA!\n$
From $400 per night (USD)
VRBO
Spacious 3BR Apartment with Patio & BBQ, Minutes from Downtown & CTA!\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our spacious 3-bedroom apartment, perfect for up to 7 guests! It features 2 bathrooms, including one with a j ...
From $400 per night (USD)
VRBO
From $471 per night (USD)
VRBO
Vital Urban: Spa Inspired Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a unique urban spa inspired retreat in Wicker Park, just a 5-minute walk from the Damen Blue Line. Named one ...
From $471 per night (USD)
VRBO
From $108 per night (USD)
VRBO
Modern and Stylish Private1BR Garden Apt in Logan Square With Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our cozy and modern West Logan Square garden apartment in one of Chicago's up-and-coming neighborhoods! The ...
From $108 per night (USD)
VRBO
From $2661 per night (USD)
VRBO
Vacation home just 2 minutes drive to Wrigley Field
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, ...
From $2661 per night (USD)
VRBO
From $96 per night (USD)
Expedia
Amazing W Loop 1BR w/ Spa, W/D, Gym, Biz Center & A/C, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Fulton Market District furnishe ...
From $96 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Stylish & Comfy 2BR/2.5BTH condo w/ Pool and Poker table near Med/United Center
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Experience the charm of this spacious "Game House," minutes from downtown Chicago and the United Center! Perfect for rel ...
From $393 per night (USD)
VRBO
From $399 per night (USD)
Expedia
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 $399 per night (USD)
Expedia
From $309 per night (USD)
VRBO
NEW! Charming 3bd Bungalow in Vibrant Andersonville by AllSet Turnover
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our vintage Andersonville bungalow! Built in the 1920s, our home exudes character with original floors, wind ...
From $309 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Vintage Arcade Apt with Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Have a great time with the entire family in this cozy apartment with games and fun for all ages. - 700 square feet - 1 ...
From $185 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Near Theaters & Nightlife, Group Fun, Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Let 'The Lush' be your group's 4BR home base for exploring the green spaces and excitement of Lincoln Park. Y ...
From $482 per night (USD)
VRBO
$4BR Steps to \L\, Explore City, For Groups$
From $485 per night (USD)
Expedia
4BR Steps to \"L\", Explore City, For Groups
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 'The Flux' is your spacious 4BR launchpad to Chicago, located just steps from the 'L' train. It's a proven fa ...
From $485 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Lincoln Park 4BR, Easy Group Trip, Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Gather your friends at 'The Glow,' a modern 4BR in a vibrant, well-connected Chicago neighborhood. Our perfec ...
From $487 per night (USD)
VRBO
From $492 per night (USD)
Expedia
4BR w/ Free Parking + Easy City Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 'The Aura' is a convenient 4BR retreat in Goose Island, perfect for family or friend getaways. Our 92% 5-star ...
From $492 per night (USD)
Expedia
From $479 per night (USD)
VRBO
4BR, Steps to Park & Fun, Family-Ready
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Designed for the perfect family getaway, 'The Nova' provides a 4BR home base with easy access to Lincoln Park's ...
From $479 per night (USD)
VRBO
From $1520 per night (USD)
Expedia
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 $1520 per night (USD)
Expedia
From $4468 per night (USD)
VRBO
Iconic Downtown Penthouses Getaway + City Views
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
Summary: 'The Lyra' pairs two exquisite penthouses for a unique Chicago experience perfect for groups seeking both leisu ...
From $4468 per night (USD)
VRBO
From $96 per night (USD)
Expedia
Blueground | South Loop 1bd apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $96 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
<b>Experience Chicago</b> Experience Chicago in this fabulous, all modern 3-bedroom 3-bath condo near Hyde Park, The Ob ...
From $300 per night (USD)
VRBO
From $273 per night (USD)
VRBO
Charming 3-bed, 3-bath house in amazing Chicago, 10 min from Midway Airport.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Discover this charming 3-bedroom gem in Chicago on a quiet tucked away street. This terrific house boasts 1 queen bed, 1 ...
From $273 per night (USD)
VRBO
Click For Pricing
VRBO
Blueground | Medical District 1bd apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Tri-Taylor with views over the city. It’ll be easy to s ...
Click For Pricing
VRBO
From $512 per night (USD)
Expedia
Blueground | River North 2bd apartment
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished two bedroo ...
From $512 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large Duplex that is pet and kid friendly. Perfect space for your whole family to enjoy your next visit to the Windy Cit ...
From $261 per night (USD)
VRBO
From $306 per night (USD)
Expedia
2 bedroom condo in North Kenwood Hyde Park with elevator.
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Your cozy getaway awaits in Chicago at this phenomenal condo. With 2 bedrooms including a king and queen bed, heating, W ...
From $306 per night (USD)
Expedia
From $310 per night (USD)
VRBO
2BR Wrigleyville Apt Free Parking, Office, Fire Pit & Outdoor Space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Chicago retreat! This cozy 2-bedroom, 1-bathroom apartment in vibrant Wrigleyville offers everyt ...
From $310 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Blueground | South Loop 1bd apartment
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 $132 per night (USD)
Expedia
From $123 per night (USD)
VRBO
Cozy Urban Retreat Near Midway – Perfect for Travelers!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Urban Cozy Midway! Nestled in the heart of Chicago’s Chicago Lawn neighborhood, this spacious 1-br apartm ...
From $123 per night (USD)
VRBO
From $153 per night (USD)
Expedia
Flexhome Wicker Park 2BR DV3
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The space: The apartment comfortably sleeps 4 with a queen bed in each room plus flexible seating areas so you can work ...
From $153 per night (USD)
Expedia
$Spacious APT near downtown | Free Assigned Parking\n\n$
From $203 per night (USD)
VRBO
Spacious APT near downtown | Free Assigned Parking\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your perfect urban retreat, where convenience meets comfort in the heart of Chicago! A short stroll away fro ...
From $203 per night (USD)
VRBO
From $234 per night (USD)
Expedia
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Looking for a spot during some Cubs games or a concert? Or just a lovely relaxing spot for a weekend in the city? YOU F ...
From $234 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Charming 3-bedroom apartment with AC and WiFi in marvelous Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Chicago is waiting for you at this 3-bedroom apartment. Each bedroom features a comfortable queen bed, perfect for a ple ...
From $255 per night (USD)
VRBO
From $233 per night (USD)
Expedia
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 $233 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Spacious 4BR/2BA – Private Sun Deck In Chicago
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Nestled in the Edgewater neighborhood of Chicago, @TheDreamRentals Skyline Escape is the perfect jumping off po ...
From $404 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Large 3 bedroom apartment in Roger’s Park!
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Welcome to our charming and elegantly updated 3BD/1BA apartment in Rogers Park! Boasting the charms of a 100 year old ...
From $277 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Four bedroom - 2 bathroom apartment
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Located in the middle of Chicago's Iconic Boystown in the Lakeview neighborhood, this four bedroom (2 queen beds, 2 full ...
From $387 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Chic studio in Loyola University with WiFi, fitness room, steps from the lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in Chicago, this charming apartment offers a superb living experience. With a cozy living room featuring a queen ...
From $199 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Stay in the heart of East Lakeview on Halsted!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom condo is in an incredibly convenient Lakeview location for all the life and culture found in Lakeview, wh ...
From $309 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Burnham King - Staypineapple Chicago Charm & Afternoon Delights in The Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $410 per night (USD)
VRBO
From $410 per night (USD)
VRBO
2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $410 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Cozy Room w/ Historic Charm & Modern Amenities in Heart of Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Elegant Room w/ Modern Conveniences & Walkable to Major Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Professionally Managed 1 Bedroom in the Chicago Loop by the Theater District
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Chicago, enjoy what this 1-bedroom apartment has to offer. This superb space features a welcoming queen bed, ...
From $185 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Cozy & Chic 2BR Loft on 18th St in Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to this apartment in picturesque Chicago. This terrific rental features 2 pleasant bedrooms with 2 queen beds, a ...
From $303 per night (USD)
VRBO
From $398 per night (USD)
Expedia
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 $398 per night (USD)
Expedia
From $96 per night (USD)
VRBO
Blueground | Streeterville, pool & gym, nr pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $96 per night (USD)
VRBO
From $104 per night (USD)
Expedia
Blueground | River North, balcony & pool, nr Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...
From $104 per night (USD)
Expedia
From $439 per night (USD)
VRBO
3 Tranquil Eco-friendly Rooms, Fitness Center, Near River North
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $439 per night (USD)
VRBO
From $295 per night (USD)
VRBO
2 Sleek Eco-friendly Rooms w/ Natural Furnishings in Vibrant River North
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $295 per night (USD)
VRBO
From $163 per night (USD)
VRBO
Experience Comfort in Eco-friendly Room w/ Earth Tone Furniture
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $163 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Relaxing Eco-friendly Room w/ Modern Decor near River North Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Cozy Eco-friendly Room w/ Earth Tone Decor, Short Walk to River North Spots
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $150 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Bedrooms:
4
Bathrooms:
8
Sleeps:
18
NEW HOME/NEWLY FURNISHED! This 8 bed home is ready to host! My space accomodates 18 guests with 10 beds and 4 full baths ...
From $620 per night (USD)
Expedia
From $99 per night (USD)
VRBO
Walk to Devon Avenue & Warren Park: Chicago Apt!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pet Friendly w/ Fee | Complimentary Snacks | 2 Mi Loyola University Nestled in Chicago's West Ridge neighborhood, with ...
From $99 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Vibrant 3BR Flamingo Paradise | Heart of Lakeview!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Discover Flamingo Paradise in the BEST location - Lakeview’s Southport Corridor! A stylish 3-bedroom, 2-bath mi ...
From $413 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Beautiful Urban Loft Style Apt* Safe Secure* Great Location* 2 Bedrooms*
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The entire 2nd floor of this completely rehabbed Chicago brick building, private entrance with intercom, Close to all ma ...
From $145 per night (USD)
VRBO
From $653 per night (USD)
Expedia
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Welcome to Your Chicago Getaway This spacious home comfortably accommodates up to 12 guests, ideal for romantic getaway ...
From $653 per night (USD)
Expedia
From $88 per night (USD)
VRBO
Blueground | West Loop, rooftop pool & gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District. It’ll be easy to simply show up ...
From $88 per night (USD)
VRBO
From $1679 per night (USD)
Expedia
Luxury Penthouse: Iconic Views + Exclusive Comfort
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Discover a premier Chicago experience in this luxury penthouse, ideal for travelers who value amazing views and ...
From $1679 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in Chicago, this brilliant apartment with 3 full beds is a dream for guests. With amenities like AC, a washing m ...
From $180 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Animal House Near Sox Stadium
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Whether your traveling with your pet or just miss a furry companion and need a loaner (just ask). Animal House is very F ...
From $156 per night (USD)
Expedia
From $205 per night (USD)
VRBO
UIC / Little Italy - Lovely 1 Bed 1 Bath Apt. - FREE PARKING & IN-UNIT WASH/DRY
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Adorable 1 bed 1 bath apartment WITH FREE PARKING AND IN-UNIT WASHER/DRYER located in the heart of Chicago's Little Ital ...
From $205 per night (USD)
VRBO
From $1079 per night (USD)
VRBO
Entire house w/ free parking, close to Wrigley!
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
We are located in prime Lakeview location, minutes to Wrigley Field, Lincoln Park, and downtown Chicago. Lakeview Chicag ...
From $1079 per night (USD)
VRBO
From $86 per night (USD)
VRBO
2 Mi to Red Line: Chicago Home Near Sherman Park
Bedrooms:
1
Bathrooms:
5
Sleeps:
9
New Kitchen Appliances | Dogs Allowed w/ Fee | Security System | 8 Mi to Grant Park Enjoy easy access to top Chicago at ...
From $86 per night (USD)
VRBO
Click For Pricing
Expedia
City View Smart, luxurious 1bd apartment - Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
City View Smart, luxurious 1BD apartment with stunning Chicago skyline views, a personalized Pilates reformer, and centr ...
Click For Pricing
Expedia
From $224 per night (USD)
VRBO
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 $224 per night (USD)
VRBO
From $117 per night (USD)
Expedia
Comfortable 2-bedroom apartment in phenomenal Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your home away from home! Comfortable apartment with an open layout, modern kitchen, and stainless steel appl ...
From $117 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Chic Chinatown Apt w parking!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $271 per night (USD)
VRBO
From $563 per night (USD)
Expedia
ChiCasa West Town Paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Stunning Chicago condo, where modern luxury meets comfort in a spacious two-level layout. Enjoy 2 cozy fireplaces, 3 bed ...
From $563 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Updated 3 Bedroom Chicago Downtown Pilsen
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Experience Chicago and Pilsen as being in the heart of 18th st. Some of the best food, music and nightlife Chic ...
From $297 per night (USD)
VRBO
From $121 per night (USD)
Expedia
Blueground | River North, pool & w/d, nr Mile
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 $121 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Gracious, spacious vintage home in a terrific neighborhood near the lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A house with real character and color. Filled with art, much by the artist who lives in it. Lots of warm oak floors and ...
From $537 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Charming 3-bedroom house with AC and WiFi in phenomenal Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Make yourself at home in this 3-bedroom Chicago retreat. This house boasts 1 queen bed and 2 full beds, perfect for a gr ...
From $177 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Blueground | Lakeshore East, pool & w/d, nr park
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 $223 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Modern 2-bedroom townhome in Chicago with private patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Welcome to the safe and peaceful Chicago neighborhood Bucktown! This property lives like a single family home and consis ...
From $387 per night (USD)
Expedia
From $432 per night (USD)
VRBO
LUXE Vintage Loft, 10min to Downtown, Retro Movie Theatre - 15% Discount Applied
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to a Luxury Vintage Getaway with a 24/7 dedicated team ensuring a comfortable and unforgettable stay. ✔ Central ...
From $432 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Blueground | Lakeshore East, pool & w/d, nr park
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 $146 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your new home away from home! This beautiful townhouse offers a cozy retreat with a queen bed and a full bed. Enjoy the ...
From $207 per night (USD)
VRBO
From $668 per night (USD)
Expedia
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $668 per night (USD)
Expedia
From $91 per night (USD)
VRBO
< 2 Mi to UChicago: Apt Near Bus Stops!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Laptop-Friendly Desk | 3 Smart TVs | 7 Mi to The Loop Nestled in the Washington Park neighborhood, this Chicago vacati ...
From $91 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Blueground | Streeterville, pool & gym, nr Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with views over the city. It’ll be easy t ...
From $149 per night (USD)
Expedia
From $119 per night (USD)
VRBO
Blueground | West Loop, pool & AC, nr Willis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this beautiful one bedroom Blueground apartment. You’ll love comin ...
From $119 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Spacious 5-bedroom/2-bathroom apartment in marvelous Chicago with AC, Wi-Fi
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Drive Times (with light traffic) 25 Min —> Downtown Chicago 15 Min —> Hyde Park 40 Min —> Indiana Dunes National Park 30 ...
From $551 per night (USD)
Expedia
From $355 per night (USD)
VRBO
McCormick 2B/2Ba with optional parking for up to 6 guests
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $355 per night (USD)
VRBO
Click For Pricing
Expedia
Minimalist Aesthetic apartment with WiFi in vibrant Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Consider this apartment your home away from home while you visit Chicago. This terrific space features a cozy bedroom wi ...
Click For Pricing
Expedia
From $317 per night (USD)
VRBO
McCormick 2B/2Ba for up to 8 guests with Skyline view and optional parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $317 per night (USD)
VRBO
From $469 per night (USD)
Expedia
53-54 Floor Penthouse
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: The Penthouses at Grand Plaza PH#B This stunning two-story Penthouse soars above Chicago, featuring dramatic li ...
From $469 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Charming 4-bedroom house with AC and WiFi in fabulous Chicago
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Discover this fantastic 4-bedroom gem in Chicago. This superb house comes equipped with all the essentials for a comfort ...
From $178 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Jefferson Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
3
Welcome to this well maintained 3 bedroom, 3 bath home in the heart of Jefferson Park filled with natural light! Large o ...
From $166 per night (USD)
VRBO
From $156 per night (USD)
VRBO
Flexhome Ukrainian Village 2BR D2
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The space: The apartment comfortably sleeps 4 and has flexible seating areas so you can work or relax at your convenienc ...
From $156 per night (USD)
VRBO
From $540 per night (USD)
VRBO
Modern Townhome in the Heart of Hyde Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Located in in the center of Hyde Park, this modern IM Pei townhome is a perfect place for your next stay in Chicago. On ...
From $540 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Chic 2-bedroom apartment in historic Chicago neighborhood with theater, Wifi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax and unwind in this comfortable, spacious and stylish 2 bedroom 2 bathroom apartment located in the heart of histor ...
From $105 per night (USD)
VRBO
From $364 per night (USD)
VRBO
Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $364 per night (USD)
VRBO
From $167 per night (USD)
VRBO
Cozy 2b2ba: 15 min Bus Downtown, 7min to UChicago, Bike to Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Cozy Study: Bronzeville 2b/2ba perfect for remote workers, students, visitors & tourists! Spacious, cozy ...
From $167 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Luxury Meets Comfort: River North Rentals with Chic Style & Prime Chicago Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $403 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Stay Chic in Chicago: River North Suites w/ Luxe Amenities & Prime Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $297 per night (USD)
VRBO
From $370 per night (USD)
VRBO
Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $370 per night (USD)
VRBO

Search Your Destination Now!

Chicago Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals