
New East Side Rentals

- From $225 per night (USD)
VRBO
La Quinta – Double Bed Room Overlooking Quiet Courtyard Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just steps from the Willis Tower, Riverwalk, and the Loop’s financial district, La Quinta Chicago Downtown offers a conv ...
From $225 per night (USD)VRBO
- From $261 per night (USD)
VRBO
La Quinta – Deluxe King Room with City Views in Chicago Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Surrounded by iconic architecture and vibrant dining, La Quinta Chicago offers city access and skyline views in the Loop ...
From $261 per night (USD)VRBO
- From $256 per night (USD)
VRBO
La Quinta – Spacious Deluxe King Room in Prime Loop Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of the Loop near Riverwalk and Millennium Park, La Quinta offers comfort and convenience for both w ...
From $256 per night (USD)VRBO
- From $236 per night (USD)
VRBO
La Quinta – Comfortable King Room in Downtown Chicago Loop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
From river cruises to museum strolls, La Quinta Chicago puts you minutes from the city's top sights and transit lines. T ...
From $236 per night (USD)VRBO
- From $275 per night (USD)
VRBO
La Quinta – King Suite with Living Area Near Chicago Landmarks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just off Wacker Drive, La Quinta provides easy access to Union Station and the Magnificent Mile. This non-smoking king s ...
From $275 per night (USD)VRBO
- From $259 per night (USD)
VRBO
La Quinta – 2 Queen Beds Room in Walkable Downtown Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $259 per night (USD)VRBO
- From $521 per night (USD)
VRBO
Convenient Stay | 2 Pet-friendly Rooms Near Willis Tower and Skydeck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $521 per night (USD)VRBO
- Click For Pricing
Expedia
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 sophisticated Chicago Loop furnished one bedr ...
Click For PricingExpedia
- From $145 per night (USD)
VRBO
Blueground | Streeterville, rooftop pool, nr Navy Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Streeterville. It’ll be easy to simply show up and start liv ...
From $145 per night (USD)VRBO
- From $524 per night (USD)
VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With ...
From $524 per night (USD)VRBO
- From $214 per night (USD)
VRBO
River North Luxury Condo 2 King Beds 2 Baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the sought-after neighborhood of River North, this 2/2 high-rise condo provides luxury accommodations with am ...
From $214 per night (USD)VRBO
- Click For Pricing
Expedia
858 Orleans
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
<p>While you're here, you can enjoy all the comforts of home and more, including a full-sized refrigerator/freezer and a ...
Click For PricingExpedia
- Click For Pricing
VRBO
Landing at 500 Lake Shore Drive - 1 Bedroom in Streeterville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
500 Lake Shore Drive was designed with your lifestyle in mind. Take a dip in the rooftop pool, then retreat from the sun ...
Click For PricingVRBO
- Click For Pricing
Expedia
Landing at 3Eleven - 1 Bedroom in River North
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
3Eleven is a popular property in the River North neighborhood of Chicago where Landing offers fully furnished studios, 1 ...
Click For PricingExpedia
- Click For Pricing
VRBO
Landing at The Regal Apartments - 2 Bedrooms in Chicago Loop
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Regal Apartments is a centrally located property in the Chicago Loop neighborhood of Chicago where Landing offers fu ...
Click For PricingVRBO
- From $650 per night (USD)
Expedia
Luxury Designer Penthouse North - 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 $650 per night (USD)Expedia
- From $531 per night (USD)
VRBO
Luxury Downtown Penthouse with Private Rooftop!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Summary: BRAND NEW REMODEL BUILT SPECIFICALLY FOR AIRBNB!! Designed by a famous Chicago Designer using strictly West El ...
From $531 per night (USD)VRBO
- From $1418 per night (USD)
Expedia
The Orleans Floor 3 Private rooftop deck!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: You will get the following with this rental: - You will have your own private floor and access to 2 individual ...
From $1418 per night (USD)Expedia
- From $1480 per night (USD)
VRBO
The Orleans - Floor 2 Private roof deck Patio!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: The Orleans - Floor 2 is custom designed for Airbnb and you will get 2 units on an entire floor of the building ...
From $1480 per night (USD)VRBO
- From $1503 per night (USD)
Expedia
Luxury Loft Collection COMBO 01/02 | Terrace
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 28
Summary: Enjoy the combination of your own 2 side-by-side private luxury lofts in Chicago's bustling River North-the cit ...
From $1503 per night (USD)Expedia
- From $665 per night (USD)
VRBO
Luxury Designer Penthouse South | 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 $665 per night (USD)VRBO
- From $1403 per night (USD)
Expedia
Luxury Designer Penthouse Combo West | 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 $1403 per night (USD)Expedia
- From $237 per night (USD)
VRBO
Amazing River North Jr 1BR w/ Game Room, nr Beach & 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 $237 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Just What You Were Looking For! Near Chicago Tribune Tower, Pets are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $700 per night (USD)VRBO
- From $254 per night (USD)
VRBO
A Place You'll Surely Enjoy! Close to Chicago Vietnam Veterans Memorial
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $254 per night (USD)VRBO
- From $306 per night (USD)
VRBO
Vacation Starts Here! Near Chicago Riverwalk and The River Theater, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $306 per night (USD)VRBO
- From $924 per night (USD)
VRBO
Downtown, Vintage 5bd/2ba (gym+patio) | Sleep 14
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! This is 2 units in a private corridor. He ...
From $924 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Level Spacious one bedroom suite with king bed, walk-in closet, full kitchen.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $175 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Level River North Luxury Two Bedroom Suite\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $289 per night (USD)VRBO
- From $273 per night (USD)
Expedia
2bd River North Condo with Million Dollar Views! by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
32+ NIGHTS MIN, *1 GARAGE PARKING SPACE INCL* Experience our stunning 49th floor River North condo! With 2 bedrooms & ...
From $273 per night (USD)Expedia
- From $301 per night (USD)
VRBO
A Place You'll Surely Enjoy! Full Kitchen, Free Breakfast, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $301 per night (USD)VRBO
- From $711 per night (USD)
VRBO
Spacious Good-Value Accommodation! 2 Convenient Units, Free Breakfast
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $711 per night (USD)VRBO
- From $229 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Free Breakfast, Near Water Tower Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $229 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Making The Best Memories Along The Way! Free Breakfast, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The property boasts a contemporary urban retreat, designed with spacious suites and fully equipped kitchens, perfect for ...
From $370 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Modern Loop Studio w/ Theater & Pool, nr Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Chicago Loop with high floor views over the city. It’ll be e ...
From $179 per night (USD)VRBO
- Click For Pricing
Expedia
420 Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
<p>While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a dishwashe ...
Click For PricingExpedia
- From $135 per night (USD)
VRBO
Amazing River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $135 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Premium Loop 1BR w/ Roof, Gym & Lounge, nr Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished one bedroom a ...
From $199 per night (USD)Expedia
- From $182 per night (USD)
VRBO
Stunning Loop 2BR w/ Gym & Doorman, same block as L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Chicago Loop furnished two bedroom apa ...
From $182 per night (USD)VRBO
- From $311 per night (USD)
VRBO
#1910 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $311 per night (USD)VRBO
- From $385 per night (USD)
VRBO
#1513 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $385 per night (USD)VRBO
- From $115 per night (USD)
Expedia
Classic Loop 1BR w/ Lounge, Gym & Roof Deck, steps to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...
From $115 per night (USD)Expedia
- From $314 per night (USD)
VRBO
#2009 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $314 per night (USD)VRBO
- From $213 per night (USD)
VRBO
#1411 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $213 per night (USD)VRBO
- From $386 per night (USD)
VRBO
#1101 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $386 per night (USD)VRBO
- From $383 per night (USD)
VRBO
#1403 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $383 per night (USD)VRBO
- From $249 per night (USD)
VRBO
Beautiful one bed room in the heart of downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the heart of river north downtown Chicago this modern styled unit is located right off the iconic Chicago Riverwalk i ...
From $249 per night (USD)VRBO
- From $188 per night (USD)
VRBO
Modern 2 Bed/1 Bath condo. Great Location and Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently remodeled modern condo in a full amenity building which includes a 24hr doorman, outdoor pool, gym, and a sunde ...
From $188 per night (USD)VRBO
- From $109 per night (USD)
VRBO
Deluxe Loop 1BR w/ Gym, Roof & Lounge, same block as L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Chicago Loop furnished one bedroom ...
From $109 per night (USD)VRBO
- From $141 per night (USD)
Expedia
Lovely Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $141 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Luxury condo close to Magnificent Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Elegance awaits! Rare 2 bed / 2 completely renovated and professionally redesigned as luxury in town residence. Lightly ...
From $246 per night (USD)VRBO
- From $201 per night (USD)
Expedia
Trendy Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $201 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Serene Loop 1BR w/ Gym, Roof & Lounge, same block as L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Chicago Loop furnished one bedroom apart ...
From $170 per night (USD)VRBO
- From $158 per night (USD)
Expedia
Classic Gold Coast 1BR w/ Deck, Gym & Lounge, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with views over the city. It’ll be easy ...
From $158 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Ideal Streeterville 1BR w/ Pool & Deck, near Beach & Park, by Blueground
- 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 $181 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Amazing Gold Coast 1BR w/ Deck, Gym & Lounge, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with views over the city. It’ll be easy ...
From $110 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Ideal Loop 1BR w/ Pool, Gym & Lounge, near Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Chicago Loop furnished one bedroom apa ...
From $139 per night (USD)VRBO
- From $309 per night (USD)
VRBO
#1409 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $309 per night (USD)VRBO
- From $168 per night (USD)
VRBO
Studio flat in the heart of Chicago's Gold Coast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Come stay in our one-bedroom studio apartment with a fully equipped kitchen and bathroom. Take in the perks of ...
From $168 per night (USD)VRBO
- From $1650 per night (USD)
Expedia
Downtown Vintage Group Lofts - Sleep 25
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 25
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Vintage Loft Suites, comprised of 4 conjoining lofts in ...
From $1650 per night (USD)Expedia
- From $780 per night (USD)
VRBO
3 Classy Units Just Minutes from Shores of Lake Michigan–Navy Pier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Make this downtown property your home base for adventure in the Windy City! Head to the rooftop deck with panoramic view ...
From $780 per night (USD)VRBO
- From $699 per night (USD)
VRBO
Group Vacation! 4 Comfortable Units, Indoor Pool, 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 $699 per night (USD)VRBO
- From $171 per night (USD)
VRBO
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 $171 per night (USD)VRBO
- From $1030 per night (USD)
VRBO
Family & Friends Escape! 4 Spacious Units, Near Magnificent Mile Shopping
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Make this downtown property your home base for adventure in the Windy City! Head to the rooftop deck with panoramic view ...
From $1030 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Windy City Getaway! Minutes to Navy Pier, Field Museum, Shedd Aquarium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Make this downtown property your home base for adventure in the Windy City! Head to the rooftop deck with panoramic view ...
From $260 per night (USD)VRBO
- From $386 per night (USD)
VRBO
#1615 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $386 per night (USD)VRBO
- From $383 per night (USD)
VRBO
#1616 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $383 per night (USD)VRBO
- From $376 per night (USD)
VRBO
#1813 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $376 per night (USD)VRBO
- From $379 per night (USD)
VRBO
#1612 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $379 per night (USD)VRBO
- Click For Pricing
Expedia
MODERN APARTMENT OVERLOOKING DOWNTOWN CHICAGO!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Unique Apartment Has A Style Of Its Own. This Fully Furnished 21st Fl Apartment Is Overlooking Michigan Ave In Down ...
Click For PricingExpedia
- From $103 per night (USD)
VRBO
Trendy Loop 1BR w/ Gym, Roof & Lounge, same block as L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $103 per night (USD)VRBO
- From $152 per night (USD)
Expedia
Sleek River North 1BR w/ Gym, Lounge & Roof, 1 block to L, by Blueground
- 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 $152 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- From $171 per night (USD)
VRBO
Prime Location! Indoor Pool, Near Millenium 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 $171 per night (USD)VRBO
- From $171 per night (USD)
VRBO
Prime Location! Indoor Pool, Near Millenium 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 $171 per night (USD)VRBO
- From $524 per night (USD)
VRBO
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 $524 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Shop ‘til you drop on the Magnificent Mile! Rooftop Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore iconic Windy City hot spots just minutes from this downtown property This listing is for a room within a hotel. ...
From $175 per night (USD)VRBO
- From $309 per night (USD)
VRBO
#1109 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $309 per night (USD)VRBO
- From $298 per night (USD)
VRBO
#1808 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $298 per night (USD)VRBO
- From $401 per night (USD)
VRBO
#2001 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $401 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Upscale Loop 2BR w/ Gym & Doorman, same block as L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $228 per night (USD)VRBO
- From $519 per night (USD)
Expedia
Downtown 3bd Penthouse| Lake Mich VIEWS +gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $519 per night (USD)Expedia
- From $284 per night (USD)
VRBO
DTown Mich Ave #10 | gym+rooftop w park view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $284 per night (USD)VRBO
- From $363 per night (USD)
Expedia
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $363 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Downtown Park #11 - Mich Ave PH | gym+rooftop
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $332 per night (USD)VRBO
- From $93 per night (USD)
Expedia
Luxe Loop Studio w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Chicago Loop furnished studio a ...
From $93 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Sleek Loop Studio w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Chicago Loop furnished one bedroom apart ...
From $216 per night (USD)VRBO
- From $474 per night (USD)
VRBO
Stylish Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic lake an ...
From $474 per night (USD)VRBO
- Click For Pricing
VRBO
Serene Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
Click For PricingVRBO
- From $112 per night (USD)
Expedia
Chic Streeterville Studio w/ Pool & Gym, nr Navy Pier, by Blueground
- 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 $112 per night (USD)Expedia
- Click For Pricing
VRBO
Lovely Loop Studio w/ Lounge & Roof, nr Riverwalk, by Blueground
- 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 ...
Click For PricingVRBO
- From $130 per night (USD)
Expedia
Sleek Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Chicago Loop furnished one bedroom ...
From $130 per night (USD)Expedia
- From $123 per night (USD)
VRBO
Lovely Loop 2BR w/ Doorman & Gym, steps to Shops, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $123 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Dreamy River North 1BR w/ Gym, Pool & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy River North furnished one bedroom apart ...
From $189 per night (USD)Expedia
- From $573 per night (USD)
VRBO
Apartment in The Loop: Great Amenities, Near Shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Don't miss out on 'The Ford', a top-choice 2BR apartment in the heart of Chicago, offering great amenities with ...
From $573 per night (USD)VRBO
- From $601 per night (USD)
Expedia
Mag Mile Retreat: Stunning Views, High-End 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy a comfortable stay in 'The Wicked', our centrally located 2BR apartment, offering stunning views of the C ...
From $601 per night (USD)Expedia
- From $622 per night (USD)
VRBO
River North 2BR: High Ceilings, Comfort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience a stylish escape in 'The Hamilton', our high-end 2BR apartment nestled in the prime location of Chic ...
From $622 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Exclusive Gold Coast 2BR: Balcony, Walkable
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience the vibrant energy of downtown Chicago from 'The Jersey', our chic 2BR apartment, ideally located st ...
From $575 per night (USD)Expedia
- From $372 per night (USD)
VRBO
Downtown Mich Ave #7| Park View Penthouse +gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $372 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Elegant Loop 1BR w/ Gym, Pool & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with balcony views over the city. It’ll be ...
From $139 per night (USD)Expedia