Cook Area Rentals
From $277 per night (USD)VRBO
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)VRBO
From $387 per night (USD)Expedia
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)Expedia
From $199 per night (USD)VRBO
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)VRBO
From $309 per night (USD)Expedia
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)Expedia
From $131 per night (USD)VRBO
Queen Studio, Hyatt House Chicago, Complimentary Breakfast, Shopping Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 485 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $131 per night (USD)VRBO
From $131 per night (USD)VRBO
Spacious Room w/ Kitchenette & Complimentary Breakfast | Free Airport Shuttle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 485 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $131 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)VRBO
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)VRBO
From $303 per night (USD)Expedia
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)Expedia
From $398 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 $398 per night (USD)VRBO
From $96 per night (USD)Expedia
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)Expedia
From $104 per night (USD)VRBO
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)VRBO
From $89 per night (USD)Expedia
Suns & Roses Duplex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful Beverly beauty is a deluxe studio apartment with a lot of natural lighting accompanied by a vibrant yello ...
From $89 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 $311 per night (USD)Expedia
3BR Tranquil Home in Tinley Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Our exquisitely furnished three-bedroom, one-bathroom home in Tinley Park, IL, is ideal for up to six people an ...
From $311 per night (USD)Expedia
From $177 per night (USD)VRBO
Day Trip to Chicago: Hoffman Estates Gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Family Friendly | Private Yard | Remote Workers Welcome Whether you’re visiting for business or simply want to experien ...
From $177 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 $410 per night (USD)VRBO
Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a recently updated home just blocks from the Rosemont Entertainment District, Casino and Convention Center, and 3 ...
From $410 per night (USD)VRBO
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)VRBO
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)VRBO
From $145 per night (USD)Expedia
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)Expedia
From $734 per night (USD)VRBO
Spacious 6-Bedroom Home, 12 beds with 2 Kitchens, Full Workout Gym, Ninja Gym & 6 Bathrooms – Perfect for Groups & Families!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
This newly renovated 6-bedroom home in Skokie is perfect for your group! Centrally located, it offers all the amenities ...
From $734 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 $460 per night (USD)Expedia
Mt. Prospect 4BR Haven Awaits
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to your home away from home in the heart of Mt. Prospect, Illinois! This inviting 4-bedroom retreat off ...
From $460 per night (USD)Expedia
From $1679 per night (USD)VRBO
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)VRBO
From $180 per night (USD)Expedia
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)Expedia
From $156 per night (USD)VRBO
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)VRBO
From $205 per night (USD)Expedia
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)Expedia
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 PricingVRBO
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 PricingVRBO
From $349 per night (USD)Expedia
Charming 3-bedroom 2-bathroom loft in Oak Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious accommodations with an upscale Oak Park loft, thoughtfully designed for modern comfort and soulful tranquility. ...
From $349 per night (USD)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 $225 per night (USD)VRBO
Tree Top View 3-bedrm Oak Park comfortable, quiet, convenient
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Oak Park from this Tree Top View next to Rehm Park, playground pool and conservatory in a fabulou ...
From $225 per night (USD)VRBO
From $117 per night (USD)VRBO
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)VRBO
From $96 per night (USD)Expedia
Beautiful 2 Bedroom located in a Unique Private Park. Near Beaches Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this brilliant 2-bedroom Chicago retreat. With 2 full beds, a cozy living space, and a bathroom ...
From $96 per night (USD)Expedia
From $512 per night (USD)VRBO
Suburban Haven: Cozy Escape with a Touch of Luxury
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
This newly updated home is the perfect place to enjoy some peace and quiet. You’ll find plenty of seating for your whole ...
From $512 per night (USD)VRBO
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 $135 per night (USD)VRBO
Modern Deluxe Studio Suite in lovely Oak Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located studio. In charming Oak Park, with a tourist friendly and trendy d ...
From $135 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 $289 per night (USD)Expedia
Private Home Awaits
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this brilliant 4-bedroom Homewood house, where guests can unwind in a tranquil setting. With amenities like a ...
From $289 per night (USD)Expedia
From $121 per night (USD)VRBO
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)VRBO
From $363 per night (USD)VRBO
Dazzling Des Plaines-Single Level Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This charming 3-bedroom, 1.5-bath ranch in Des Plaines offers comfort and convenience. The fully stocked kitchen is perf ...
From $363 per night (USD)VRBO
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 $188 per night (USD)VRBO
Modern Airport Oasis -Minutes from O'Hare Airport and Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space: Relax in simplicity at this peaceful, centrally located spot. Just 15 minutes from O'Hare airport, 20 ...
From $188 per night (USD)VRBO
From $432 per night (USD)Expedia
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)Expedia
From $146 per night (USD)VRBO
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)VRBO
From $207 per night (USD)Expedia
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)Expedia
From $668 per night (USD)VRBO
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)VRBO
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 $204 per night (USD)VRBO
Just Updated! Charming 3-bedroom 25 Minutes from Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Burbank, this charming house offers 3 bedrooms with a king, queen, and twin bed. Just a short drive from Chi ...
From $204 per night (USD)VRBO
From $250 per night (USD)Expedia
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Oak Park, this delightful apartment is a brilliant choice for guests seeking a cozy retreat. With 2 bedrooms ...
From $250 per night (USD)Expedia
From $149 per night (USD)VRBO
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)VRBO
From $119 per night (USD)Expedia
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)Expedia
From $551 per night (USD)VRBO
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)VRBO
From $355 per night (USD)Expedia
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)Expedia
Click For PricingVRBO
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 PricingVRBO
From $317 per night (USD)Expedia
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)Expedia
From $185 per night (USD)VRBO
Roomy 2 bedroom Long-term Stay Apartment in Oak Park near downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your home away from home. Step into this beautiful, top-floor, 2-bedroom apartment, offering the perfect blen ...
From $185 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
From $385 per night (USD)VRBO
Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & 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 $385 per night (USD)VRBO
From $504 per night (USD)VRBO
Chic River North Retreat: Luxe Suites, Stunning Views, Steps from Chicago Life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $504 per night (USD)VRBO
From $723 per night (USD)VRBO
Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $723 per night (USD)VRBO
From $193 per night (USD)VRBO
5 Mi to Dtwn: Ukrainian Village Apartment!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Walk to Restaurants | Sleek Furnishings Make the most of your next Windy City adventure when you book this updated Chic ...
From $193 per night (USD)VRBO
From $425 per night (USD)VRBO
House with garage, outdoor dining and basement bar
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this superb house in picturesque Chicago. With 4 queen beds spread across 4 bedrooms and 3 bathrooms equipped ...
From $425 per night (USD)VRBO
From $230 per night (USD)Expedia
Two Bedroom - Tranquil Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our enchanting 2-bedroom, 1-bathroom haven nestled in the vibrant heart of Wrightwood, Chicago. Ideal for fam ...
From $230 per night (USD)Expedia
From $648 per night (USD)VRBO
Peaceful Oasis - Captivating Six-Bedroom Escape
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Discover the charm of Wrightwood, Chicago, from the comfort of our enchanting 6-bedroom, 3-bathroom rental haven. You wi ...
From $648 per night (USD)VRBO
From $597 per night (USD)Expedia
Charming house in Oak Park. Free parking. 15 mins to downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Chicago at its finest is just a stay away. Enjoy the luxury of being a mere 15 mins from downtown Chicago with a peacef ...
From $597 per night (USD)Expedia
From $179 per night (USD)VRBO
Stylish and Cozy 2BR, Family Friendly, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this beautifully remodeled, modern 2-bedroom, 1-bathroom apartment, perfectly situated in the lively and dive ...
From $179 per night (USD)VRBO
From $259 per night (USD)Expedia
Gold Coast 2 Bedroom Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern 2BR Retreat in Gold Coast – Stylish & Newly Renovated! Experience the best of Chicago’s Gold Coast in this brand ...
From $259 per night (USD)Expedia
From $212 per night (USD)VRBO
Blueground | West Loop, gym & bbq, nr Willis Tower
- 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 $212 per night (USD)VRBO
From $164 per night (USD)VRBO
Light-filled 1bdrm garden apartment on golf course near Northwestern U.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Whether you are in town for a Northwestern Football game or graduation or want to be closer to all that Evanston and Lak ...
From $164 per night (USD)VRBO
From $521 per night (USD)VRBO
Your Chicago Home Base – 4BR, 2BA, Sleeps 15, Ideal for Families & Groups!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to Your Chicago Home Away from Home! This spacious and modern 4-bedroom, 2-bathroom home comfortably sleeps up ...
From $521 per night (USD)VRBO
From $420 per night (USD)Expedia
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Free garage parking!!! Fabulous and expansive! 4 bedroom and 3 full bathroom apartment set in trendy Humboldt Park. The ...
From $420 per night (USD)Expedia