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 $489 per night (USD)
VRBO
Spacious 3br home near Chicago, fenced yard for pets
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Modern Family Home in Quiet Neighborhood - Close to Chicago Welcome to our spacious 2800 sqft single-family home, perfe ...
From $489 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Cozy 2-Bedroom Apartment with WiFi, AC & More in Hip Logan Square
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming apartment is designed for comfort and convenience, giving you the perfect place to relax after a day of ex ...
From $178 per night (USD)
Expedia
From $1308 per night (USD)
VRBO
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Bedrooms:
5
Bathrooms:
10
Sleeps:
26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1308 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Charming 2-bedroom 1 bathroom Bridgeport Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes heating, an ...
From $194 per night (USD)
VRBO
From $280 per night (USD)
VRBO
Chic 2-bedroom apartment with AC, WiFi in vibrant Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a soothing stay at this 2-bedroom apartment in Chicago. The cozy space features 2 queen beds, WiFi, AC, and heatin ...
From $280 per night (USD)
VRBO
From $193 per night (USD)
Expedia
3-bedroom apt .on North Side! Great location between downtown and the airport.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Discover this 3-bedroom gem in Chicago. Remodeled basement unit apartment in the Belmont Cragin neighborhood. Central No ...
From $193 per night (USD)
Expedia
From $119 per night (USD)
VRBO
Chicago Apt 3 Mi to Lake Michigan!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
10 Mi to Downtown Chicago | Private Deck | 1,875 Sq Ft Get to know the Windy City up close and personal while staying a ...
From $119 per night (USD)
VRBO
From $257 per night (USD)
VRBO
Suite Dreams • Designer Style • Central • Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Stylish Home Base in Pilsen: Modern 3BR/2BA condo located in the vibrant East Pilsen/University Village ...
From $257 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Dream Stay - Modern Bungalow Near Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautiful bungalow in Home Sweet Homewood with upscale decor and finishes. Stay comfortably in this 4-bedroom house. Wit ...
From $527 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Downtown 2bd #6 +Gym near Park, Lake, Museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $291 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Downtown 2bd #5 +Gym near Park, Lake, Museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $291 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Downtown 3bd #7 near Park+Museums
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $410 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Charming 3-bedroom house with AC and WiFi in awesome Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom Chicago retreat. This charming house offers all the comforts you need for a wond ...
From $271 per night (USD)
VRBO
From $1184 per night (USD)
Expedia
Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Relax with the whole family or explore the city with friends at this peaceful and spacious 6 bedroom duplex conversion. ...
From $1184 per night (USD)
Expedia
From $444 per night (USD)
VRBO
West Loop 2BR, Walk to Top Restaurants, Sleeps 5
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Aqua' is your comfortable 2-bedroom apartment in the West Loop neighborhood. It's a peaceful home with eas ...
From $444 per night (USD)
VRBO
From $474 per night (USD)
Expedia
West Loop PH: Unmatched Views & Private Deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Ideal for families and business travelers seeking spacious luxury in Chicago's West Loop. Our last five guest ...
From $474 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Explore Fulton Market + Retreat in Modern Comfort
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Experience the vibrant heart of Fulton Market at 'The Neo', ideal for sophisticated travelers seeking scenic vi ...
From $533 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Stylish 2BR Retreat in Fulton Market for Getaways
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Experience the perfect blend of design and location at 'The Deco', ideal for sophisticated travelers seeking le ...
From $530 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Exclusive 3BR with Views, Ideal for Tourists
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 'The Rose' offers spacious urban living, steps from Millennium Park. With 90% of our reviews at 5 stars since 2 ...
From $729 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Prime Loop Luxury + City & Train Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: 'The Daisy' offers a unique blend of luxury and convenience, perfect for business travelers and tourists. As ...
From $392 per night (USD)
Expedia
From $702 per night (USD)
VRBO
High-End 3BR Retreat + Steps to Millennium Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 'The Tulip' offers a luxurious escape near top attractions, hosted by a professional team with a 5-year Superho ...
From $702 per night (USD)
VRBO
From $245 per night (USD)
Expedia
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
Spacious 1200 sqft 3BR 1BA located 10-15 min from Downtown! Tub/Shower Games for adults & kids 5 Smart TVs, free fast wi ...
From $245 per night (USD)
Expedia
From $460 per night (USD)
VRBO
Prime Lincoln Park Views + Modern Amenities Await
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Elm' is your luxury retreat for the ultimate urban getaway, with scenic views and a location that puts eve ...
From $460 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Lincoln Park Getaway: Skyline Views & Luxury
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Pine' is the perfect home base for your Chicago adventure. Top dining and city transit are just outside yo ...
From $483 per night (USD)
Expedia
From $944 per night (USD)
VRBO
Premium 2BR Apartments in Lincoln Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: For families and large groups, 'The Ash' makes your Chicago stay easy, offering two spacious apartments with Wh ...
From $944 per night (USD)
VRBO
From $666 per night (USD)
Expedia
Prime 4BR Penthouse w/ Skyline Views for Families
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Your family's perfect Chicago retreat awaits at 'The Soul,' a spacious 4BR penthouse featuring a kids' room, tw ...
From $666 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Skyline Views in 3BR Apartment w/ Top Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience top-tier comfort in 'The Frame,' the perfect spacious home base for your travels. Don't just take ...
From $526 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Sky-High 2BR w/ Gym & City Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Discover ultimate relaxation at 'The Avant,' perfect for tourists seeking a vibrant stay in Fulton Market. Ou ...
From $533 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Modern 2BR in The Loop + Panoramic City Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Looking for a spotless stay in the heart of the action? 'The Violet' delivers, with unmatched city access and a ...
From $570 per night (USD)
VRBO
From $1025 per night (USD)
VRBO
Event Proximity + Unique Group Retreat in Loop
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Discover 'The Lotus,' your group's private sanctuary in the city, with two stylish apartments placing you steps ...
From $1025 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Top-Floor Oasis: 2BR in Heart of Fulton Market
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Welcome to 'The Dada,' where urban sophistication meets art-filled design. Enjoy premier amenities and the top- ...
From $538 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Chic Fulton Market Oasis + Curated Comfort & Style
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Boho' offers skyline views and resort-style amenities for tourists seeking a unique Chicago getaway. Boo ...
From $531 per night (USD)
Expedia
From $1224 per night (USD)
VRBO
Ideal for Groups: Spacious 2BR in The Loop
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: Discover 'The Poppy,' your group's vibrant home base in The Loop, offering two stylish apartments with breathta ...
From $1224 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Stylish 2BR with Skyline Views Near Riverwalk
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to 'The Pine,' your stylish home base in the heart of the Windy City. You can relax in total comfort kn ...
From $525 per night (USD)
Expedia
From $1428 per night (USD)
VRBO
Downtown Penthouse Huge Patio with Great View
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Immerse yourself in comfort with our 3600 sqft unit, featuring a 1400 sqft balcony and stunning city panoramas. This spa ...
From $1428 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Downtown 2bd #4 - Near Grant Park, Museums, Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $292 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Stylish 3BR + Free Parking 15-20mins from Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cozy Family-Friendly Apartment Near Downtown Chicago Welcome to our modern, spacious 3-bedroom apartment, ideal for fam ...
From $286 per night (USD)
VRBO
From $1337 per night (USD)
Expedia
Wrigley 4BR Home, Sleeps 10, Firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience Wrigley Ville in this spacious 4-bedroom, 2-bath home, perfect for groups. The house combines two units, offe ...
From $1337 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Wrigleyville 2BR w/Parking, Firepit & Workspace for Remote Work
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the charm of Chicago’s North Side in this cozy 2-bedroom, 1-bathroom apartment, just steps from iconic Wrigley ...
From $484 per night (USD)
VRBO
From $126 per night (USD)
Expedia
Brand New 3B-2BA Unit,4 miles from Downtown Chicago with WiFi, AC, Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your Hestia Certified home in the heart of Chicago! Discover the beauty of Chicago from this 3-bedroom 2-bath ...
From $126 per night (USD)
Expedia
From $441 per night (USD)
VRBO
High-End West Loop 2BR + City Views & Walkability
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Ideal for tourists and business travelers, 'The Terra' boasts a perfect location for city exploration. With 1 ...
From $441 per night (USD)
VRBO
From $431 per night (USD)
Expedia
West Loop Oasis: Skyline Views + Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Flame' is your perfect Chicago base for an unforgettable adventure, complete with a private balcony and ex ...
From $431 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Prime 2BR Retreat: Urban Vibes + Views Await
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Lotus' offers an unbeatable downtown experience for urban explorers, complete with remarkable city views a ...
From $572 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Cozy 3-bedroom condo near University of Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come experience this newly renovated, reclaimed red brick 1895 colonial multi-family building. Located 5 mins from the U ...
From $292 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Get ready to relax in this lovely, updated 3-bedroom house in Crestwood. With 1 king bed, 2 queen beds, and 1 full bed ( ...
From $222 per night (USD)
VRBO
From $184 per night (USD)
VRBO
Retro Apt-Downtown Palatine-Big Sofa-King Bed-Private Deck-Laundry-Parking-Train
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
MId Century Modern 1 Bedroom With Private Entrance in Downtown Palatine! Over 140 5 Star Reviews ★★★★★ "I cannot say e ...
From $184 per night (USD)
VRBO
From $397 per night (USD)
VRBO
Stylish Escape/Game Room/4 Brs
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Escape to our cozy 4-bedroom, 2-bath ranch house, just 1 mile from Arlington Height downtown restaurants and 25 miles fr ...
From $397 per night (USD)
VRBO
From $310 per night (USD)
Expedia
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come stay at our luxurious downtown view in a new construction in Chicago. This centrally located, gated, 3Bedroom, 3Bed ...
From $310 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $114 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Spacious 5-bedroom house with movie room, game room and more!
Bedrooms:
2
Bathrooms:
5
Sleeps:
16
Located in Berwyn, this house is a dream. With 5 bedrooms including 4 queen beds and 2 full beds, this peaceful retreat ...
From $558 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Spacious 2BR | Quiet Long-Term Stays | Niles, IL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy space, privacy, and peace of mind in this 2-bedroom home located in a quiet, residential neighborhood in Niles, Il ...
From $187 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Welcome to Rainbow Guest House. This is a designer owned, fully decorated house located in a perfect Bucktown/Wicker Par ...
From $1001 per night (USD)
Expedia
From $435 per night (USD)
VRBO
1 Garage Parking/Skyline Rooftop/PingPong/Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax in this stunning 2-bedroom, 2-bath condo for up to 8 guests, featuring a king bed, one double bed and one ...
From $435 per night (USD)
VRBO
From $175 per night (USD)
VRBO
2-bedroom haven near Ohare with Wi-Fi, AC in fabulous Bellwood
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this adorable condo in picturesque Bellwood. This perfect getaway features 2 cozy bedrooms with queen beds, a ...
From $175 per night (USD)
VRBO
From $406 per night (USD)
VRBO
33rd-Floor Penthouse with Breathtaking Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience 'The Harper', a prime 3BR penthouse with panoramic skyline views, perfect for discerning travelers s ...
From $406 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This central location can't be beat! Situated on the border of Lakeview and Wrigleyville and only 1 mile from historic ...
From $187 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Dual Penthouse Retreat: Perfect for Groups
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: The premier choice for corporate retreats and family reunions, 'The Adler' offers two stunning penthouses that ...
From $659 per night (USD)
VRBO
From $400 per night (USD)
Expedia
4 bedrooms, 6 beds, 2 full baths, and open basement loft
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
4 bedrooms, 6 beds, 2 full baths, and open basement loft. Your family of 10+ persons will be close to everything when yo ...
From $400 per night (USD)
Expedia
From $329 per night (USD)
VRBO
Breeze of Bronzeville Chicago: 3 bedroom 2 bath 9 mins from downtown chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Chicago with 3 adorable queen bedrooms. This charming house offers WiFi, a washing machine, ...
From $329 per night (USD)
VRBO
From $321 per night (USD)
VRBO
Charming 3-bedroom house in Calumet City with WiFi and AC
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to our simple but stylish retreat just 15 minutes away from the vibrant city of Chicago. This sleek and modern s ...
From $321 per night (USD)
VRBO
Click For Pricing
VRBO
Spacious 3-bedroom apartment in lovely CHICAGO Ukranian VILLAGE w/laundry
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Newly redesigned first floor unit with a sleek, minimalist approach. Equipped with brand new appliances, comfy beds, str ...
Click For Pricing
VRBO
From $632 per night (USD)
Expedia
Radiance - 4BR Single Level Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to your home away from home! This inviting 4-bedroom, 2.5-bathroom retreat is nestled in the heart of S ...
From $632 per night (USD)
Expedia
From $669 per night (USD)
VRBO
Tranquility 4BR Schaumburg
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Summary: Welcome to your home away from home! Our spacious 5-bedroom retreat in the heart of Schaumburg, IL, is perfect ...
From $669 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Spacious & Modern 3BD/2BA Home- Garage Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Chicago’s lively River West & West Loop, you’re just minutes away from some of Chicago’s best d ...
From $397 per night (USD)
Expedia
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 $245 per night (USD)
Expedia
Cozy house in the city
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Experience Burbank like a local in this enchanting 3-bedroom house. Step inside and be greeted by an adorable living spa ...
From $245 per night (USD)
Expedia
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)
VRBO
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)
VRBO
From $393 per night (USD)
Expedia
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)
Expedia
From $399 per night (USD)
VRBO
Spacious 4-bedroom house in fabulous Chicago Back Yard Pond, and Theatre
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Chicago is waiting for you at this 4-bedroom house. With 2 queen beds, 1 bunk bed, and 1 twin bed, this lovely property ...
From $399 per night (USD)
VRBO
From $309 per night (USD)
Expedia
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)
Expedia
From $185 per night (USD)
VRBO
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)
VRBO
From $482 per night (USD)
Expedia
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)
Expedia
$4BR Steps to \L\, Explore City, For Groups$
From $485 per night (USD)
VRBO
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)
VRBO
From $487 per night (USD)
Expedia
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)
Expedia
From $492 per night (USD)
VRBO
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)
VRBO
From $479 per night (USD)
Expedia
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)
Expedia
From $1520 per night (USD)
VRBO
PH w/ Bean & Lake Views, An Elite Stay
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The ...
From $1520 per night (USD)
VRBO
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)
VRBO
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)
VRBO
From $300 per night (USD)
Expedia
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)
Expedia
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
Expedia
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
Expedia
From $512 per night (USD)
VRBO
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)
VRBO
From $261 per night (USD)
Expedia
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)
Expedia
From $306 per night (USD)
VRBO
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)
VRBO
From $310 per night (USD)
Expedia
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)
Expedia
From $132 per night (USD)
VRBO
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)
VRBO
From $123 per night (USD)
Expedia
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)
Expedia
From $153 per night (USD)
VRBO
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)
VRBO
$Spacious APT near downtown | Free Assigned Parking\n\n$
From $203 per night (USD)
Expedia
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)
Expedia
From $234 per night (USD)
VRBO
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)
VRBO
From $255 per night (USD)
Expedia
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)
Expedia
From $233 per night (USD)
VRBO
Jumbo 3bd In Hot Logan Square!
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Bring the whole family to this great place with lots of room for fun Comfortable 1100 sqft 3 BR 1 BA located in the beau ...
From $233 per night (USD)
VRBO
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 $145 per night (USD)
VRBO
Hyatt House Schaumburg Suite, 1-Bedroom Kitchen, 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 $145 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Relaxing 1BR Suite w/ Living Area | Outdoor Pool Access and Free Breakfast
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 $145 per night (USD)
VRBO

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