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

Chicago Rentals

From $310 per night (USD)
VRBO
North Chicago Spacious Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 4 bedrooms, and is step ...
From $310 per night (USD)
VRBO
From $179 per night (USD)
VRBO
West Loop Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Fantastic unit in the 6th floor of a full amenity building hosting gorgeous views of the city. Locating in the center of ...
From $179 per night (USD)
VRBO
From $214 per night (USD)
VRBO
Spacious 3BR Family Stay w/ Central Air & Patio; Near Lakefront and UChicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Clean, comfortable, and made for connection—enjoy summer in Chicago with friends and family. Stay cool with central air ...
From $214 per night (USD)
VRBO
From $921 per night (USD)
Expedia
Sleeps 18 • 8BR • Game Room • Gym • Theater
Bedrooms:
3
Bathrooms:
8
Sleeps:
18
Welcome to your ultimate 8BR escape—where engaging entertainment meets thoughtful comfort. The arcade-style game room in ...
From $921 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Blissful Chicago Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a beautiful apartment only a short walk away from Clark street which features amazing nightlife and some of the ...
From $230 per night (USD)
VRBO
From $370 per night (USD)
Expedia
Mid-Century Modern 2 BD APT | Walk to Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience stylish comfort in this beautifully designed, mid-century modern apartment in the heart of Wrigleyville. Enjo ...
From $370 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Amazing Location 3BR Gem in Logan Square w Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Prime location in Logan Square! Steps away from numerous top-tier restaurants, cafes, the square itself, and a plethora ...
From $304 per night (USD)
VRBO
From $987 per night (USD)
VRBO
2 Designer Apts for Group Stays + Top Amenities
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Perfect for your next group trip or corporate offsite, 'The Pop' offers two same-floor apartments for the ultim ...
From $987 per night (USD)
VRBO
From $1454 per night (USD)
VRBO
Luxury Designer Penthouse Combo | NW | Gold Coast
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1454 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Cozy 3BR with Parking Easy Access Lake Shore Dr
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Discover the hidden gems and welcoming atmosphere of Chicago's West Ridge neighborhood when you stay at this centrally-l ...
From $269 per night (USD)
VRBO
From $1170 per night (USD)
VRBO
This holiday home is a 4 bedroom(s), 2 bathrooms, located in Chicago, IL.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, ...
From $1170 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Game Day Getaway - 3BR in Vibrant Wrigleyville
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
An excellent location in the vibrant heart of Wrigleyville! It's a brief 5-minute stroll to Wrigley Field and just aroun ...
From $437 per night (USD)
VRBO
From $997 per night (USD)
VRBO
Modern 6BR House Steps to Wrigleyville
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Fantastic location in the heart of Wrigleyville! Just a 5-minute walk to Wrigley Field and a block from The Metro concer ...
From $997 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Bright & Modern 3BR/1BA in Logan Square
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Prime Logan Square Locale! Steps away from premier restaurants, cafes, the square, and abundant entertainment options. C ...
From $436 per night (USD)
VRBO
From $539 per night (USD)
VRBO
Explore the City: Sleek 2BR Gem in North Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the historic charm of North Side Chicago at our cozy residence. Tucked away in a quiet neighborhood with tree-l ...
From $539 per night (USD)
VRBO
From $418 per night (USD)
VRBO
Chic Studio with WiFi and AC in Beautiful Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Greatly situated in Logan Square! Just a stone's throw away from excellent restaurants, cafes, the square itself, and an ...
From $418 per night (USD)
VRBO
From $324 per night (USD)
VRBO
Loyola Lookout – Sporty 3BR Apt Steps from Loyola & Lake w/ Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sporty Style Meets City Comfort – Steps from Loyola, the Lake & the L! Welcome to your home base in Chicago’s vibrant Ro ...
From $324 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Prime Location! 3BRGem near University of Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our home is located in the desirable Southside neighborhood of Chicago. The area is known for its vibrant culture, diver ...
From $275 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Cozy Retreat, Prime Location Near Loyola & Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy the ideal mix of comfort and convenience in this cozy 1BR/1BA Airbnb, just steps from Loyola University and Lake M ...
From $154 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 $191 per night (USD)
VRBO
Charming 3-bedroom smart house in fabulous Chicago with AC, WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Nestled in Chicago, this delightful smart house offers 3 cozy bedrooms - 2 with queen beds and 1 with a sofa bed. The ba ...
From $191 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 $414 per night (USD)
VRBO
South Loop Three Bedroom Two Bath Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Conveniently located near McCormick Place and Soldier Field. Close to parks, shopping, and public transportatio ...
From $414 per night (USD)
VRBO
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 $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 $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 $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 $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 $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 $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 $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 $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 $307 per night (USD)
VRBO
Chic Modern NEW Loft near United Center, UIC/IMD & Downtown W/ Street Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Discover luxury in our newly renovated 2nd floor loft in Tri-Taylor. With 13-ft ceilings, large windows, brick and moder ...
From $307 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 $716 per night (USD)
VRBO
Luxury Two-Level Townhouse | Patio | Lincoln Park
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Summary: NEWLY RENOVATED TOWNHOUSE IN THE HEART OF LINCOLN PARK! This private luxury townhouse (duplex) is perfectly lo ...
From $716 per night (USD)
VRBO
From $394 per night (USD)
VRBO
Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and ...
From $394 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Cozy Chinatown Apartment w free parking spot!
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 $295 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Spacious, one-level condo next to Jackson Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...
From $333 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Chic 2-bedroom apartment in vibrant Chicago with AC, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the beauty of Chicago from this 2-bedroom apartment. This delightful space features 1 bunk bed and 1 full bed, ...
From $407 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This styl ...
From $400 per night (USD)
VRBO
From $1192 per night (USD)
VRBO
Luxury Designer Penthouse Combo |North| Gold Coast
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1192 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Charming Chicago Apt
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Discover comfort and convenience in this spacious two-bedroom, two-bath apartment, ideally designed to accommod ...
From $218 per night (USD)
VRBO
From $946 per night (USD)
VRBO
Wrigleyville 3BD Condo
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $946 per night (USD)
VRBO
From $1025 per night (USD)
VRBO
Wrigleyville Garden 3BR/9beds Pod
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1025 per night (USD)
VRBO
From $2304 per night (USD)
VRBO
Six-Bedrooms in Wrigleyville
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...
From $2304 per night (USD)
VRBO
From $1116 per night (USD)
VRBO
Luxury Designer Penthouse Combo |South| Gold Coast
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1116 per night (USD)
VRBO
From $250 per night (USD)
VRBO
3 Bedroomin the Medical Center!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: A couple houses off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Fu ...
From $250 per night (USD)
VRBO
From $319 per night (USD)
VRBO
South Loop 4 Bedroom apt
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
Summary: South Loop 4 bedroom apartment with 1.5 bathrooms. We are centrally located and very easy to get anywhere in th ...
From $319 per night (USD)
VRBO
From $460 per night (USD)
VRBO
Chic 2BR 2BA Condo with Balcony - River North Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Per ...
From $460 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Quick Drive to Downtown Chicago & Early Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Book your stay now at our modern, fully furnished condo—just minutes from downtown Chicago and the Illinois Medical Dist ...
From $240 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Luxury Designer Penthouse West |Pool| Gold Coast
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...
From $530 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Updated 3 Bedroom Chicago Historic Andersonville
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $322 per night (USD)
VRBO
From $714 per night (USD)
VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
✨ I highly recommend this location. The home is beautiful and quaint. The location is perfect. The neighbor is very quie ...
From $714 per night (USD)
VRBO
From $664 per night (USD)
Expedia
Luxury Loft Collection 703 - Terrace - River North
Bedrooms:
3
Bathrooms:
3
Sleeps:
14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...
From $664 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Family, Groups - Convenient to Wrigley, Loop, Airport - Spacious 2200 Sq Ft
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $392 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Stylish 2BR Urban Retreat in River West
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Welcome to our contemporary 2-bedroom, 1-bathroom condo in lively River West. Ideal for business and leisure, t ...
From $249 per night (USD)
VRBO
From $324 per night (USD)
VRBO
Wrigleyville Suites Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $324 per night (USD)
VRBO
$Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n$
From $396 per night (USD)
VRBO
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...
From $396 per night (USD)
VRBO
From $151 per night (USD)
VRBO
2BD/1 BA with summer patio in quiet Roscoe Village
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $151 per night (USD)
VRBO
From $236 per night (USD)
VRBO
❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome to Chicago! Whether you’re in town to seal a business deal or have a short holiday breather, our warm three-bed ...
From $236 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Bright 3BR/1BA FREE Parking/Laundry in Pilsen. Minutes from Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Escape to the vibrant heart of Pilsen and experience Chicago like a local in our charming home: -Fully equipped, modern ...
From $185 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Perfect 2BD/1BA FREE Garage Parking/Laundry in Pilsen. Minutes to downtown.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover our 2-bed, 1-bath Pilsen gem! Adorned with local art, a workspace, and free parking & laundry, it's minutes fro ...
From $192 per night (USD)
VRBO
From $386 per night (USD)
VRBO
Chic River North Condo 2BR 2BA with Private Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Welcome to our riverfront oasis nestled in the vibrant heart of Chicago's trendy River North neighborhood! Thi ...
From $386 per night (USD)
VRBO
From $206 per night (USD)
Expedia
A Home Away From Home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover the allure of this newly renovated Georgian house. Boasting ample space for family enjoyment. With its close pr ...
From $206 per night (USD)
Expedia
From $254 per night (USD)
VRBO
River North Central Home With Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Enjoy a stylish experience at @TheDreamRentals centrally-located home in Chicago's River West neighborhood. Rel ...
From $254 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Fulton market / Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...
From $306 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...
From $414 per night (USD)
VRBO
From $289 per night (USD)
Expedia
The Norwood Nook – Walkable Stay Near O’Hare & Metra!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
- Upper unit within two-unit building - 5 miles to O’Hare Airport - 10 minute drive without traffic - Blackout curtains ...
From $289 per night (USD)
Expedia
From $127 per night (USD)
VRBO
Hip South Loop 1BR w/ Gym & Game Room, nr Top Schools, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $127 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...
From $223 per night (USD)
Expedia
From $894 per night (USD)
VRBO
The Grand Kimball Lodge, Logan Square, Sleeps 14
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: Welcome to The Grand Kimball Lodge, a truly unique getaway featured in Architectural Digest's "21 Best Chicago ...
From $894 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Stunning Suite 2 @ Hotel Nemo Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...
From $118 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Sunny Lakeview 1BR w/ Rooftop & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $204 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Open Lakeview 2BR w/ Gym & Grills, nr Lakefront Trail, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Lake View East with balcony views over the city. It’ll ...
From $364 per night (USD)
Expedia
From $92 per night (USD)
VRBO
Dreamy Streeterville Studio w/ Pool & Gym, nr Navy Pier, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $92 per night (USD)
VRBO
From $84 per night (USD)
Expedia
Deluxe Loop 1BR w/ Gym & Doorman, nr L & Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $84 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Open Loop 2BR w/ Lounge & Gym, nr Chicago Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
From $199 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Amazing Streeterville 2BR w/ Gym & Pool, Ohio St beach, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Streeterville furnished two bedroom ...
From $329 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Long-Term Stays | 1 Garage Parking | Private Balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to our vacation home! Nestled in the heart of the city, it offers the perfect blend of sophistication a ...
From $318 per night (USD)
VRBO
From $128 per night (USD)
VRBO
Walk to Train & Bus: Updated Chicago Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
5 Mi to Midway | Close to Hospitals | On Main Road in Residential Area Your extended stay in Chicago is made easy at th ...
From $128 per night (USD)
VRBO
From $89 per night (USD)
VRBO
Deluxe Edgewater 1BR w/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $89 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Splendid Corner 3BR in the Loop | City Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $527 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Gorgeous South Loop 2BR w/ Jacuzzi & Rooftop, nr Colleges, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in South Loop with balcony views over the city. It’ll be e ...
From $207 per night (USD)
VRBO
From $756 per night (USD)
VRBO
Luxury Retreat with Home Theater
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Summary: Welcome to @TheDreamRentals opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the c ...
From $756 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Chic 4-Bedroom Haven: Designer's Dream Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: Welcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home ...
From $452 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Ideal South Loop 2BR w/ Pool, Gym & Rooftop, nr L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished two bedroom apart ...
From $197 per night (USD)
Expedia
From $52 per night (USD)
VRBO
Home sweet home in Northwest Chicago, almost a sole unit for you, great location
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Full cozy, clean, and private garden suite for a pleasant stay. The home is located on a beautiful tree-lined residentia ...
From $52 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Fremont St. Guesthouse - Unit 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Classic Chicago Brownstone, updated 3 bedroom and 2 bathroom high end, 1st floor condo. Located on beautiful Fremont Str ...
From $449 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Beautiful Downtown 3BR with Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
A beautiful and modern three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'l ...
From $423 per night (USD)
VRBO
From $229 per night (USD)
Expedia
The Neighborhood Hotel - Little Italy One Bedroom - ADA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM ADA This airy, one bedroom suite exudes a mid-century Italian meets slee ...
From $229 per night (USD)
Expedia
From $217 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Studio
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
1 KING BED + 1 BATHROOM This airy studio exudes a mid-century Italian meets sleek urban loft vibe. Pops of color compli ...
From $217 per night (USD)
VRBO
From $375 per night (USD)
Expedia
The Neighborhood Hotel - Little Italy Two Bedroom w/ Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + BALCONY This airy, two bedroom suite exudes a mid-centur ...
From $375 per night (USD)
Expedia
From $314 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy Two Bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM This airy, two bedroom suite exudes a mid-century Italian ...
From $314 per night (USD)
VRBO
From $267 per night (USD)
Expedia
The Neighborhood Hotel - Little Italy Two Bedroom - ADA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 KING BED + 1 QUEEN BED + 1 QUEEN SLEEPER SOFA + 1 ADA BATHROOM This airy, two bedroom suite exudes a mid-century Ital ...
From $267 per night (USD)
Expedia
From $268 per night (USD)
VRBO
The Neighborhood Hotel - Little Italy One Bedroom w/ Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
1 KING BED + 1 QUEEN SLEEPER SOFA + 1 BATHROOM + PATIO This airy, one bedroom suite exudes a mid-century Italian meets ...
From $268 per night (USD)
VRBO
From $748 per night (USD)
VRBO
Pilsen Paradise l 3 miles to DT
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: Welcome to our 2-in-1 retreat in Pilsen! Two side-by-side apartments with modern, sleek finishes and fully stoc ...
From $748 per night (USD)
VRBO
From $434 per night (USD)
VRBO
Chic River North Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our Chic River North Retreat, a hidden gem in vibrant River North, Chicago. Discover a rare 2-bedroo ...
From $434 per night (USD)
VRBO
From $410 per night (USD)
VRBO
STYLISH-LOCAL-COMFY-SAFE 5 night min.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Conveniently located in Chicago to all of Chicago. Located in Chicago’s Andersonville & Edgewater area. Down the stre ...
From $410 per night (USD)
VRBO
From $285 per night (USD)
VRBO
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $285 per night (USD)
VRBO
$Luxéry Stay \Hollywood\ Downtown/McCormick/WinTrust Area$
From $828 per night (USD)
Expedia
Luxéry Stay \"Hollywood\" Downtown/McCormick/WinTrust Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience the best of Chicago from this stunning 3-bedroom apartment in the South Loop. With its elegant desig ...
From $828 per night (USD)
Expedia

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