Cook Area Rentals
From $145 per night (USD)VRBO
Landing | Beautiful 1BD, Yoga Studio, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $145 per night (USD)VRBO
From $155 per night (USD)Expedia
Landing | Spectacular 1BD, Yoga Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $155 per night (USD)Expedia
From $179 per night (USD)VRBO
Landing | Stunning 1BD, Rooftop Lounge, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $179 per night (USD)VRBO
From $134 per night (USD)Expedia
Landing | Chic 1BD, Yoga Studio, Rooftop Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Lydian in Chicago, IL! Perfect for monthly or extended stays, our fully furnished apartments feature full ...
From $134 per night (USD)Expedia
From $178 per night (USD)VRBO
Landing | Modern 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $178 per night (USD)VRBO
From $171 per night (USD)Expedia
Landing | Amazing 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $171 per night (USD)Expedia
From $188 per night (USD)VRBO
Landing | Stunning 1BD in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $188 per night (USD)VRBO
From $164 per night (USD)Expedia
Landing | Stylish Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $164 per night (USD)Expedia
From $132 per night (USD)VRBO
Landing | Incredible Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $132 per night (USD)VRBO
From $172 per night (USD)Expedia
Landing | Stylish Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $172 per night (USD)Expedia
From $163 per night (USD)VRBO
Landing | Modern Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $163 per night (USD)VRBO
From $164 per night (USD)Expedia
Landing | Amazing Studio in Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Inside Info Fremont in Chicago, IL! Perfect for monthly or extended stays, our fully-furnished apartments fea ...
From $164 per night (USD)Expedia
From $461 per night (USD)VRBO
Luxe 3BR + Patio & Parking | Sleeps 9 | Lakeview
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: You'll feel it the moment you walk in — this isn't a typical rental. It's a sprawling, light-filled home on on ...
From $461 per night (USD)VRBO
From $667 per night (USD)Expedia
Spacious Chicago Group Home! Walk to Train & Eats
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Game Room + Yard | 7 Mi to Downtown | Bring Your Pets This 3-bed Chicago vacation rental is perfect for families and gr ...
From $667 per night (USD)Expedia
From $201 per night (USD)VRBO
By Wrigley Field +Reserved Parking Space +95 Walkscore + In-Unit Laundry + Patio
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Top host approved all-new construction luxury condo in a quaint 3-unit building that sleeps 5 and offers great natural l ...
From $201 per night (USD)VRBO
From $211 per night (USD)Expedia
Flexhome West Town Spacious 2BR Duplex · Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover the best of Chicago from this spacious 2-bedroom, 2-bathroom duplex apartment. Whether you`re in town for a con ...
From $211 per night (USD)Expedia
From $282 per night (USD)VRBO
Luxury Fulton Market Condo - Prime Location Walking distance to Riverwalk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay in the heart of Chicago’s West Loop. One block from Fulton Market’s award winning restaurants, bars, and cafés. Clo ...
From $282 per night (USD)VRBO
From $148 per night (USD)Expedia
Private Covered Garage +In-Unit Laundry+ Restaurant Row+93 Walkscore + 606 Trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nicknamed "Midwest Headquarters of Hip" Logan Square was voted one of the coolest places in the country by Cushman & Wak ...
From $148 per night (USD)Expedia
From $206 per night (USD)VRBO
Top Rated w/Free Street Parking+ 2 King Beds 1 Single +In Unit-Laundry +1.5 Bath
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Newly renovated, Scandinavian inspired, apartment with all the amenities we have noted that guests desire in a home away ...
From $206 per night (USD)VRBO
From $407 per night (USD)Expedia
Spacious 4BR near Northwestern with King Beds + Crib
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Centrally located just 10 minutes from Northwestern University, it’s perfect for family trips, graduations, and easy acc ...
From $407 per night (USD)Expedia
From $550 per night (USD)VRBO
Huge 5BR Heart of Fulton Market, Duplex of dreams
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your spacious duplex located in the Heart of Fulton Market, one of Chicago’s most exciting and sought-after n ...
From $550 per night (USD)VRBO
From $186 per night (USD)Expedia
South Loop 2BR Oasis w/ Patio & Gym Near McCormick Place and Soldier Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a modern 2-bedroom corner suite in Chicago’s highly sought-after South Loop, just a short walk from McCormick ...
From $186 per night (USD)Expedia
From $138 per night (USD)VRBO
Historic 1930s Retreat! Walk to Wicker Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Restored Funeral Home | Pet Friendly w/ Fee | Walk to Public Transit | WFH Ready Experience a one-of-a-kind stay at thi ...
From $138 per night (USD)VRBO
From $403 per night (USD)Expedia
NEW! Stylish 3BD/2.5BTH w/parking! United Center!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Book your next Windy City getaway at this 3-bed, 2.5-bath Chicago vacation rental. Perfect for families or friends, this ...
From $403 per night (USD)Expedia
From $310 per night (USD)VRBO
CHICAGO Portage Park Pad
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Traveling alone or with the family this apartment has the space to lounge rest or work. Located in a quite residential n ...
From $310 per night (USD)VRBO
From $129 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this spacious The Loop furnished one bedroom apart ...
From $129 per night (USD)VRBO
From $109 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- 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 $109 per night (USD)VRBO
From $808 per night (USD)Expedia
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our bright and modern 4-bedroom corporate suite in the heart of Chicago. Designed for both comfort ...
From $808 per night (USD)Expedia
From $744 per night (USD)VRBO
Modern 3BR Apartment Near North Ave Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitch ...
From $744 per night (USD)VRBO
From $174 per night (USD)Expedia
Cozy 2-bedroom condo near O'Hare/Train/Pet OK/Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy this home away from home! * Convenient location – Close to the airport with easy access to downtown, just a short ...
From $174 per night (USD)Expedia
From $872 per night (USD)VRBO
Charming 5-bedroom Jefferson Park Bungalow near O’Hare
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Consider this bungalow your home away from home while you visit Chicago. This marvelous retreat features five spacious b ...
From $872 per night (USD)VRBO
From $162 per night (USD)Expedia
Modern Berwyn Retreat - 15 Min to Midway - Easy Access to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in this modern Berwyn apartment near Downtown Chicago and Midway Airport, ideal for families, couples, small groups ...
From $162 per night (USD)Expedia
From $381 per night (USD)VRBO
O’Hare 7-Bed Home | Workers & Insurance
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Comfortable 4BR/2BA home in Des P ...
From $381 per night (USD)VRBO
From $365 per night (USD)Expedia
Family Haven in Streamwood | Ideal for Stay Long
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 10
Welcome to your family-friendly extended-stay retreat in Streamwood! This inviting 4-bedroom, 3-bathroom home is perfect ...
From $365 per night (USD)Expedia
From $365 per night (USD)VRBO
Westchester Corporate Stay 5 Beds
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
The whole group will enjoy easy access to everything from this centrally located place. Comfortable 3BR Corporate Housi ...
From $365 per night (USD)VRBO
From $110 per night (USD)VRBO
Blueground | West Loop, rooftop, nr Union Park
- 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 $110 per night (USD)VRBO
From $590 per night (USD)VRBO
Huge 4BR+4BTH Penthouse in West Town Hotspot!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your perfect Chicago home base w/Free Parking! Stay in a newer construction 4 Bedroom / 4 Full Bathroom Pent ...
From $590 per night (USD)VRBO
From $119 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- 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 $119 per night (USD)VRBO
From $117 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish The Loop furnished one bedroom apartm ...
From $117 per night (USD)VRBO
From $112 per night (USD)VRBO
Blueground | West Loop, rooftop, nr Union Station
- 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 $112 per night (USD)VRBO
From $106 per night (USD)VRBO
Blueground | Little Italy, pool, nr National Museum of Mexican Art
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Little Italy. It’ll be easy to simply show up and start ...
From $106 per night (USD)VRBO
From $103 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in The Loop. It’ll be easy to simply show up and start living i ...
From $103 per night (USD)VRBO
From $133 per night (USD)VRBO
Blueground | Chicago Loop, pool, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in The Loop. It’ll be easy to simply show up and start liv ...
From $133 per night (USD)VRBO
From $100 per night (USD)VRBO
Blueground | Edgewater, fitness center, nr Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...
From $100 per night (USD)VRBO
From $126 per night (USD)VRBO
Blueground | Edgewater, fitness center, nr Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Edgewater. It’ll be easy to simply show up and start li ...
From $126 per night (USD)VRBO
From $166 per night (USD)VRBO
Blueground | Central Station, pool, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Central Station furnished two bedro ...
From $166 per night (USD)VRBO
From $76 per night (USD)VRBO
Blueground | Goose Island, view, nr Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy studio Blueground apartment. You’ll love coming home to ...
From $76 per night (USD)VRBO
From $100 per night (USD)VRBO
Blueground | West Loop Gate, rooftop, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright West Loop Gate furnished one bedroom a ...
From $100 per night (USD)VRBO
From $95 per night (USD)VRBO
Cozy 2 Bed Apt - Midway Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Newly rehabbed 2 bedroom 1 bathroom lower level apartment less than 5 miles from Midway Airport. 10 min ...
From $95 per night (USD)VRBO
From $105 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish West Loop Gate furnished one bedroom ...
From $105 per night (USD)VRBO
From $97 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this comfortable one bedroom Blueground apartment. You’ll love com ...
From $97 per night (USD)VRBO
From $96 per night (USD)VRBO
Blueground | West Loop, pool, nr Union Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in West Loop Gate. It’ll be easy to simply show up and start li ...
From $96 per night (USD)VRBO
From $102 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated studio Blueground apartment. You’ll love coming ...
From $102 per night (USD)VRBO
From $270 per night (USD)Expedia
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Waveland Chicago 544 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...
From $270 per night (USD)Expedia
From $180 per night (USD)VRBO
Adorable 1-bedroom building with AC in beautiful Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Make yourself at home in this 1-bedroom Chicago retreat. This adorable building offers a cool space where guests can rel ...
From $180 per night (USD)VRBO
From $100 per night (USD)Expedia
Charming 1-bedroom apartment in enchanting Evanston with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Evanston at this amazing apartment. This welcoming space features a comfortable bedroom, hea ...
From $100 per night (USD)Expedia
From $505 per night (USD)VRBO
Serene 2-bedroom condo with AC in vibrant Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Chicago, this delightful condo offers guests a comfortable stay with two cozy bedrooms featuring a queen bed ...
From $505 per night (USD)VRBO
From $152 per night (USD)Expedia
Cozy 2-bedroom apartment on top floor in the heart of Ukrainian Village with AC.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable apartment is the perfect, charming home base for your trip to Chicago. In the heart of Ukrainian Village, ...
From $152 per night (USD)Expedia
From $243 per night (USD)VRBO
Chicago Stay Near Midway Airport & Orange Line
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Windy City Nest, a cozy 1-bedroom retreat in Archer Heights, Chicago. Enjoy a clean, modern space designed fo ...
From $243 per night (USD)VRBO
From $108 per night (USD)VRBO
Blueground | Fulton Market District, pool, nr Union Park
- 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 $108 per night (USD)VRBO
From $235 per night (USD)VRBO
River North Stay | 1 Unit | Near Chicago Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago's vibrant River North neighborhood, this hotel offers easy access to downtown attractions such as the ...
From $235 per night (USD)VRBO
From $212 per night (USD)Expedia
Spacious 1BR - Free Parking, Golf & Midway Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
More Space. Free Parking. Unbeatable Location. Skip the cramped city stays — this spacious 1-bedroom Chicago apartment ...
From $212 per night (USD)Expedia
From $382 per night (USD)VRBO
Minutes to Wrigley - Games Arcades - Patio - Sleeps 12
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 12
1000 sq feet 2nd floor unit 3BR 1BA In the heart of beautiful, fun, and safe Lakeview East/Wrigley Located minutes from ...
From $382 per night (USD)VRBO
From $423 per night (USD)Expedia
Spacious Westchester Duplex for Group & Family
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to your stylish and ultra-comfortable home away from home in Westchester, IL. This large, modern duplex offers p ...
From $423 per night (USD)Expedia
From $253 per night (USD)VRBO
Chicago Boutique Hideaway • Private Deck, Fire Pit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: A rare private outdoor deck with fire pit—your own cozy escape. Tucked away behind a historic Chicago home, ...
From $253 per night (USD)VRBO
From $328 per night (USD)VRBO
Boutique Retreat • Private Patio + Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Maison Jardin Soleil! A historic home built in 1885 and recently updated for timeless charm and m ...
From $328 per night (USD)VRBO
From $212 per night (USD)VRBO
NEW! Bright Modern 3Bed 2.5Bath Evanston Home w/Parking by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
**Hosting 30+ Night Reservations** Welcome to our modern two story home in Evanston! With 3 bedrooms, 2.5 baths and ...
From $212 per night (USD)VRBO
From $151 per night (USD)VRBO
Blueground | Cabrini-Green, pool, nr Chicago River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this bright one bedroom Blueground apartment. You’ll love coming h ...
From $151 per night (USD)VRBO
From $358 per night (USD)VRBO
Lincoln Park Apt: Walk to Beach, Shops & Dining!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to this charming 1-bedroom, 2-bath vacation rental in the heart of Lincoln Park! Located near top attractions lik ...
From $358 per night (USD)VRBO
From $1216 per night (USD)Expedia
Steps to Lake & Beach! Multi-Level Oakland Haven
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
3 Mi to McCormick Place & Museum Campus | 4 Mi to Downtown | Fire Pit + BBQ | Basketball Court Experience the perfect b ...
From $1216 per night (USD)Expedia
From $482 per night (USD)VRBO
Classic Forest Park Foursquare < 1 Mi to Blue Line
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Pet Friendly w/ Fee | 2 Blocks to Shops & Eats | 10 Mi to Downtown Chicago Book this Forest Park vacation rental and se ...
From $482 per night (USD)VRBO
From $444 per night (USD)Expedia
Spacious 4BR-2.5 bath Family-Friendly Retreat sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience a spacious retreat in a quite subdivision located right in the heart of famous suburbs Schaumburg . Location ...
From $444 per night (USD)Expedia
From $235 per night (USD)VRBO
Prime Location! Near Millennium Park, Shedd Aquarium, Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $235 per night (USD)VRBO
From $683 per night (USD)Expedia
2 Spacious Units Close to Navy Pier! Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $683 per night (USD)Expedia
From $235 per night (USD)VRBO
Downtown Chicago Stay | 1 King Bed | Near River North
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Chicago’s vibrant River North neighborhood, this hotel offers easy access to top attractions like the Magnifi ...
From $235 per night (USD)VRBO
From $996 per night (USD)Expedia
Group Vacation! 4 Comfortable Units, Rooftop Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 4 separate rooms withi ...
From $996 per night (USD)Expedia
From $230 per night (USD)VRBO
River North Stay | 1 Unit | Near Chicago Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Chicago's River North neighborhood, this hotel offers easy access to popular attractions like the Magnificent ...
From $230 per night (USD)VRBO
From $749 per night (USD)Expedia
Recharge & Relax! Three Comfortable Units for Group Travel Near Willis Tower
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 3 separate rooms withi ...
From $749 per night (USD)Expedia
From $500 per night (USD)VRBO
Vacation Day Is Always A Great Idea! Two Great Units, Close to Willis Tower
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for 2 separate rooms withi ...
From $500 per night (USD)VRBO
From $235 per night (USD)Expedia
Perfect Destination! Onsite Bar and Restaurant, Close to Shedd Aquarium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $235 per night (USD)Expedia
From $101 per night (USD)VRBO
Blueground | West Loop Gate, pool, nr Union Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop Gate. It’ll be easy to simply show up and sta ...
From $101 per night (USD)VRBO
From $145 per night (USD)VRBO
Blueground | Cabrini-Green, pool, nr Riverwalk
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Cabrini-Green furnished one bedroom apar ...
From $145 per night (USD)VRBO
From $110 per night (USD)VRBO
Blueground | Chicago Loop, rooftop, nr Millennium Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in The Loop. It’ll be easy to simply show up and start liv ...
From $110 per night (USD)VRBO
From $111 per night (USD)VRBO
Blueground | Little Italy, pool, nr Union Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Little Italy. It’ll be easy to simply show up and start ...
From $111 per night (USD)VRBO
From $133 per night (USD)VRBO
3 Bedroom Chicago Apartment w/ Large Kitchen & In-Unit Laundry
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Unwind in Chicago at this delightful apartment. With 3 bedrooms featuring a king bed, heating, in-unit laundry, and wind ...
From $133 per night (USD)VRBO
From $777 per night (USD)Expedia
3BR Art Deco retreat with garage.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This thoughtfully designed 1,400 sq ft residence is just a 1-minute walk from Wrigley Field. Blending historic character ...
From $777 per night (USD)Expedia
From $131 per night (USD)VRBO
Blueground | Rush & Division, rooftop, nr Lake Shore
- 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 $131 per night (USD)VRBO
From $171 per night (USD)VRBO
Blueground | Rush & Division, rooftop, nr Lakefront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this spacious two bedroom Blueground apartment. You’ll love coming ...
From $171 per night (USD)VRBO
From $130 per night (USD)VRBO
Blueground | Central Station, pool, nr Grant Park
- 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 $130 per night (USD)VRBO
From $207 per night (USD)VRBO
Blueground | Rush & Division, rooftop, nr Lake Shore Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this spacious Gold Coast furnished two bedroom apa ...
From $207 per night (USD)VRBO
From $118 per night (USD)VRBO
Blueground | Central Station, pool, nr Grant Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Central Station furnished one bedro ...
From $118 per night (USD)VRBO
From $310 per night (USD)Expedia
Cozy 3BR Retreat with grill • Near O’Hare Airport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your comfortable 3BR retreat in Des Plaines, Illinois — a peaceful and convenient home located just 7 minutes ...
From $310 per night (USD)Expedia
From $299 per night (USD)VRBO
Spacious Modern 3BR • Top‑Floor + Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Recharge in Your Edgewater Oasis Spacious modern top‑floor 3BR with a private street‑facing deck and an enclosed sunroom ...
From $299 per night (USD)VRBO
From $109 per night (USD)Expedia
Luxury Furnished Garden Unit in North Park. Stylish, Modern & Peaceful
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is available for 32+ day stays only (mid-term rental)! Kick back and relax in this calm, stylish space. Th ...
From $109 per night (USD)Expedia
From $766 per night (USD)VRBO
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to affluential Bronzeville neighborhood. Bronzeville jazz room is a luxury living space. Designed for small grou ...
From $766 per night (USD)VRBO
From $468 per night (USD)Expedia
1 Free Parking, Gym, Balcony, Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Stunning 3 bedroom West Loop apartment with 1 Garage Parking Space, Private Balcony with 1 king bed, 2 full be ...
From $468 per night (USD)Expedia
From $1454 per night (USD)VRBO
Spacious 6 BR Villa, Birthday, Events, Sleeps 20
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
Planning an elegant birthday, anniversary or a reunion? Experience unmatched, peace & luxury at this exclusive 5,000 sq ...
From $1454 per night (USD)VRBO
From $234 per night (USD)Expedia
Spacious 3BR Near United Center & Medical District
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your stylish Chicago home designed for comfort, convenience, and easy city access. This modern 3-bedroom, 2-b ...
From $234 per night (USD)Expedia
From $495 per night (USD)VRBO
6 King Bed Duplex with Pool Table - Sleeps 16
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to your spacious 6-bedroom duplex in Chicago, designed for families, friends and group travelers who want comfor ...
From $495 per night (USD)VRBO
From $126 per night (USD)Expedia
Bright & Quiet 2 Bd Nest / 1st FL Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Our peaceful apartment is the perfect home base for your trip to Chicago. Guests will find two comfortable bedrooms, fea ...
From $126 per night (USD)Expedia