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

New East Side Rentals

From $93 per night (USD)
VRBO
Upscale Living, Deluxe King, The Chicago Hotel Collection Magnificent Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $93 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Shop Chicago and Relax by The Bean | City Viwes | 24-hour Gym | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $187 per night (USD)
VRBO
From $193 per night (USD)
VRBO
City Center, Saint Clair Suite - The Chicago Hotel Collection Magnificent Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $193 per night (USD)
VRBO
From $83 per night (USD)
VRBO
Windy City Hideaway | Mag Mile Magic | Navy Pier | Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $83 per night (USD)
VRBO
From $93 per night (USD)
VRBO
Modern Digs Steps from Mag Mile Shops/Dining with 24-hour Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $93 per night (USD)
VRBO
From $94 per night (USD)
VRBO
Shop Chicago’s Magnificent Mile – Steps Away from Navy Pier - Bar On-Site
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $94 per night (USD)
VRBO
From $281 per night (USD)
VRBO
Rooms for the Crew | 3 units | Steps to Mag Mile| Navy Pier | 24-hour Gym
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $281 per night (USD)
VRBO
From $281 per night (USD)
VRBO
The Chicago Hotel Collection Magnificent Mile, Modern Double Queen, 3 Units
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $281 per night (USD)
VRBO
From $167 per night (USD)
VRBO
The Chicago Hotel Collection Magnificent Mile, Modern Double Queen | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $167 per night (USD)
VRBO
From $2870 per night (USD)
VRBO
Luxury Loft Collection 1, 2, 3
Bedrooms:
9
Bathrooms:
9
Sleeps:
42
Summary: Enjoy the combination of your own 3 side-by-side-by-side private luxury lofts in Chicago's bustling River North ...
From $2870 per night (USD)
VRBO
From $204 per night (USD)
VRBO
Elegant King Bed 1.5 Bath Suite in the Heart of Chicago's Gold Coast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each apartment offers a luxurious living experience, as they come fully furnished with all the amenities you could need. ...
From $204 per night (USD)
VRBO
From $2368 per night (USD)
Expedia
870 bldg - 3 Separate Suites in same building
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Summary: This listing is ideal for LARGE GROUPS that wish to have individual Suites and separate living spaces for diffe ...
From $2368 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Chicago Cityview Chic - Gold Coast/River North
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our stylish, modern 2-bed, 1-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover ...
From $190 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Luxury Loft Collection 902 - 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 build ...
From $759 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $196 per night (USD)
VRBO
From $196 per night (USD)
VRBO
Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $196 per night (USD)
VRBO
From $158 per night (USD)
VRBO
Historic and Unique Brownstone in Gold Coast - 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...
From $158 per night (USD)
VRBO
From $322 per night (USD)
Expedia
3rd Floor Flat in River North - 3N
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
Summary: REMODELED AND BUILT SPECIFICALLY FOR AIRBNB. The entire property is designed by a famous Chicago Designer us ...
From $322 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Beautiful Unit CHI in Prime River North - 1
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This is a super unique place! This Downtown Living destination is perfect for everything from families with sma ...
From $532 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Deluxe 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 $244 per night (USD)
Expedia
From $486 per night (USD)
VRBO
3BR Luxury Modern Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most ...
From $486 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Chicago Cityview Chic II Gold Coast/River North
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...
From $269 per night (USD)
Expedia
Click For Pricing
VRBO
Large Modern 2BD/2BA Condo in River North- Free Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our chic 2 bedroom, 2 bath condo (Parking Included) in the heart of River North, one of the most sought-after ...
Click For Pricing
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 $410 per night (USD)
VRBO
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)
VRBO
From $729 per night (USD)
Expedia
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)
Expedia
From $392 per night (USD)
VRBO
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)
VRBO
From $702 per night (USD)
Expedia
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)
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 $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 $1620 per night (USD)
VRBO
3 Stylish 2BRs Steps from Magnificent Mile
Bedrooms:
6
Bathrooms:
6
Sleeps:
15
Summary: Designed for a comfortable group getaway, 'The Mary' offers a modern and spacious retreat in the renowned Gold ...
From $1620 per night (USD)
VRBO
From $1453 per night (USD)
VRBO
3 Central Apartments Ideal for Groups
Bedrooms:
5
Bathrooms:
7
Sleeps:
15
Summary: The ideal solution for your next corporate offsite, 'The Dahlia' offers spacious and sophisticated accommodatio ...
From $1453 per night (USD)
VRBO
From $572 per night (USD)
Expedia
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)
Expedia
From $1388 per night (USD)
VRBO
High-end Luxury Units + Iconic Views for Groups
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
Summary: Ideal for groups, 'The Apollo' offers two stylish apartments in a prime location, just steps from Chicago's bes ...
From $1388 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Two 2BRs Near Millennium Park, Ideal for Groups
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Gather your favorite people at 'The Winfrey,' our exclusive offering of two luxury apartments, perfect for your ...
From $551 per night (USD)
VRBO
From $1153 per night (USD)
VRBO
Gold Coast Group Retreat + Breathtaking Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Discover the perfect group retreat in Chicago's Gold Coast, a collection of two modern 2BR apartments with priv ...
From $1153 per night (USD)
VRBO
From $114 per night (USD)
Expedia
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)
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 $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 $238 per night (USD)
VRBO
Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Burnham King - Staypineapple Chicago Charm & Afternoon Delights in The Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)
VRBO
From $410 per night (USD)
VRBO
Burnham Two Queen - Stylish Comfort by the Theatre District, 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $410 per night (USD)
VRBO
From $410 per night (USD)
VRBO
2 Inviting Rooms for Groups w/ Afternoon Delights Near Millennium Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $410 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Atwood Queen at Staypineapple - Pet-Friendly Bliss Near Millennium Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Cozy Room w/ Historic Charm & Modern Amenities in Heart of Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $197 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Elegant Room w/ Modern Conveniences & Walkable to Major Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Burnham Two Queen - Staypineapple's Historic Charm Next to Navy Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 172 sq. ft, equipped with complimentary toiletries, high defi ...
From $208 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Professionally Managed 1 Bedroom in the Chicago Loop by the Theater District
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Chicago, enjoy what this 1-bedroom apartment has to offer. This superb space features a welcoming queen bed, ...
From $185 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Luxury Designer Penthouse|Private Deck|Gold Coast
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's ce ...
From $529 per night (USD)
VRBO
From $96 per night (USD)
Expedia
Blueground | Streeterville, pool & gym, nr pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the city. It’l ...
From $96 per night (USD)
Expedia
From $104 per night (USD)
VRBO
Blueground | River North, balcony & pool, nr Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished one bedroom apar ...
From $104 per night (USD)
VRBO
From $439 per night (USD)
VRBO
3 Tranquil Eco-friendly Rooms, Fitness Center, Near River North
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $439 per night (USD)
VRBO
From $295 per night (USD)
VRBO
2 Sleek Eco-friendly Rooms w/ Natural Furnishings in Vibrant River North
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $295 per night (USD)
VRBO
From $163 per night (USD)
VRBO
Experience Comfort in Eco-friendly Room w/ Earth Tone Furniture
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $163 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Relaxing Eco-friendly Room w/ Modern Decor near River North Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
VRBO
Cozy Eco-friendly Room w/ Earth Tone Decor, Short Walk to River North Spots
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $150 per night (USD)
VRBO
From $1679 per night (USD)
VRBO
Luxury Penthouse: Iconic Views + Exclusive Comfort
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Discover a premier Chicago experience in this luxury penthouse, ideal for travelers who value amazing views and ...
From $1679 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Blueground | The Loop, pool & gym, nr park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Chicago Loop furnished one bedroom apar ...
From $203 per night (USD)
Expedia
From $121 per night (USD)
VRBO
Blueground | River North, pool & w/d, nr Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $121 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Blueground | Lakeshore East, pool & w/d, nr park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $223 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Blueground | Lakeshore East, pool & w/d, nr park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $146 per night (USD)
VRBO
From $149 per night (USD)
Expedia
Blueground | Streeterville, pool & gym, nr Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with views over the city. It’ll be easy t ...
From $149 per night (USD)
Expedia
From $469 per night (USD)
VRBO
53-54 Floor Penthouse
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: The Penthouses at Grand Plaza PH#B This stunning two-story Penthouse soars above Chicago, featuring dramatic li ...
From $469 per night (USD)
VRBO
From $364 per night (USD)
VRBO
Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $364 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Luxury Meets Comfort: River North Rentals with Chic Style & Prime Chicago Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $403 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Stay Chic in Chicago: River North Suites w/ Luxe Amenities & Prime Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $297 per night (USD)
VRBO
From $385 per night (USD)
VRBO
Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $385 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Chic River North Retreat: Luxe Suites, Stunning Views, Steps from Chicago Life!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $504 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $723 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Gold Coast 2 Bedroom Hideaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern 2BR Retreat in Gold Coast – Stylish & Newly Renovated! Experience the best of Chicago’s Gold Coast in this brand ...
From $259 per night (USD)
Expedia
From $1356 per night (USD)
VRBO
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Bedrooms:
4
Bathrooms:
6
Sleeps:
26
RENT WITH CONFIDENCE FROM A PREMIER HOST WITH OVER 800 POSITIVE REVIEWS! One-of-a-kind opportunity to rent a historic Gi ...
From $1356 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Heart of Chicago, Double Queen @ The Chicago Hotel Collection Magnificent Mile
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $187 per night (USD)
VRBO
From $249 per night (USD)
VRBO
The Chicago Hotel Collection Magnificent Mile Upscale Saint Clair Suite, 3 Units
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $249 per night (USD)
VRBO
From $167 per night (USD)
VRBO
City Center Luxury, Double Queen - The Chicago Hotel Collection Mag Mile
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $167 per night (USD)
VRBO
From $83 per night (USD)
VRBO
The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $83 per night (USD)
VRBO
Click For Pricing
Expedia
Blueground | River North, pool & AC, nr Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Near North furnished one bedroom apa ...
Click For Pricing
Expedia
From $141 per night (USD)
VRBO
Blueground | River North, pool & AC, nr Mile
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Near North furnished one bedroo ...
From $141 per night (USD)
VRBO
From $106 per night (USD)
Expedia
Blueground | The Loop, elevator, nr Willis Tower
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Chicago Loop furnished one bedroom ap ...
From $106 per night (USD)
Expedia
From $560 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 $560 per night (USD)
VRBO
From $337 per night (USD)
VRBO
The Ultimate Chicago Experience! Close to Chicago Riverwalk and Picasso Statue
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 $337 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Ideal Mix of Comfort and Value! 2 Comfortable Units, Near Marina City!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $380 per night (USD)
VRBO
From $589 per night (USD)
VRBO
4 Spacious Units Close to Navy Pier and Willis Tower! Parking, Pets Allowed!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $589 per night (USD)
VRBO
From $148 per night (USD)
VRBO
Perfect for your Chicago Getaway! Close to Midway Airport! Onsite Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $148 per night (USD)
VRBO
From $148 per night (USD)
VRBO
Beach Getaway! Minutes to Street Beach and Ohio Street Beach! Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $148 per night (USD)
VRBO
From $558 per night (USD)
VRBO
Better Choice for your Vacation! 3 Convenient Units, Close to Chicago Riverwalk
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $558 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Group Vacation! 2 Spacious Units Near Oak Street Beach! Onsite Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located on the Magnificent Mile in River North Chicago, this room is within walking distance of the Old Post Office and ...
From $294 per night (USD)
VRBO
From $1173 per night (USD)
VRBO
Longterm living in Chicago: 3BR Luxury Lakefront@Oak St Beach--pool, gym, decks
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Escape to this luxury 2200sf condo in Chicago, on a high floor with lake views, pool and deck. This gorgeous condo boast ...
From $1173 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Nestled in the heart of Chicago, this delightful apartment offers a tranquil escape for guests. With a cozy bedroom feat ...
From $255 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $449 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Walk Everywhere! 5 mins to Magnificent Mile, River
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience Chicago in style from this modern River North retreat, perfectly positioned for exploring the city's ...
From $282 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Walk Everywhere! 5 mins to Magnificent Mile, River
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience Chicago in style from this modern River North retreat, perfectly positioned for exploring the city's ...
From $281 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Walk Everywhere! 5 mins to Magnificent Mile, River
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience Chicago in style from this modern River North retreat, perfectly positioned for exploring the city's ...
From $275 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Luxurious King Suite Offering Comfort and Style in Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 398 sq. ft, equipped with complimentary toiletries, high defi ...
From $291 per night (USD)
VRBO
From $302 per night (USD)
VRBO
Relax in a Spacious King Suite with Stunning Views of Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 395 sq. ft, equipped with complimentary toiletries, high defi ...
From $302 per night (USD)
VRBO
From $301 per night (USD)
VRBO
Reliance King Suite at Staypineapple, An Iconic Hotel, The Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 395 sq. ft, equipped with complimentary toiletries, high defi ...
From $301 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Millennium Park King Suite at Staypineapple, An Iconic Hotel, The Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 398 sq. ft, equipped with complimentary toiletries, high defi ...
From $291 per night (USD)
VRBO

Search Your Destination Now!

New East Side Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 378 Rentals