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

Click For Pricing
VRBO
Upscale Streeterville Studio w/ Dog Run & Deck, near Park, 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 ...
Click For Pricing
VRBO
From $501 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 $501 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 Pricing
VRBO
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 Pricing
VRBO
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 $592 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 $592 per night (USD)
VRBO
From $598 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 $598 per night (USD)
Expedia
From $621 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 $621 per night (USD)
VRBO
From $574 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 $574 per night (USD)
Expedia
From $353 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 $353 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
From $193 per night (USD)
VRBO
Ideal Loop 2 BR w/ Gym & Doorman, 3 blocks from Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this stylish two bedroom Blueground apartment. You’ll love coming ...
From $193 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Downtown Charm: 2BR, Comfort, Great Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Your perfect place for an upscale stay in downtown Chicago awaits! 'The Hudson' is a modern two-bedroom apartme ...
From $611 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Modern 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 lovely River North furnished one bedroom apar ...
From $105 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Bright River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $128 per night (USD)
Expedia
From $104 per night (USD)
VRBO
Spacious 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 sophisticated River North furnished one bedro ...
From $104 per night (USD)
VRBO
From $367 per night (USD)
VRBO
#1413 - 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 $367 per night (USD)
VRBO
From $264 per night (USD)
VRBO
#2010 - 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 $264 per night (USD)
VRBO
From $514 per night (USD)
VRBO
#1802 - 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 $514 per night (USD)
VRBO
From $297 per night (USD)
VRBO
#1110 - 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 $297 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Premium Gold Coast 2BR w/ Gym & Lounge, 1 block to L, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Rush & Division with balcony views over the city. It’ll ...
From $178 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Dreamy River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
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 $189 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Urban Retreat: 2BR, Resort Amenities, Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Your perfect place awaits in the heart of Chicago at 'The Kroc', a thoughtful design landmark that promises an ...
From $570 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Dreamy Loop 1BR w/ Gym & Doorman, same block as 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 $182 per night (USD)
VRBO
From $580 per night (USD)
Expedia
River North 2BR: Balcony, Walk to Mag Mile, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Discover a comfortable stay with breathtaking skyline views from the private balcony of 'The Addams', our 2BR a ...
From $580 per night (USD)
Expedia
From $537 per night (USD)
VRBO
The Loop 2BR: Historic, Modern Luxury, Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Your top priority in Chicago is an iconic stay at 'The Jones', a high-end apartment that perfectly blends histo ...
From $537 per night (USD)
VRBO
From $306 per night (USD)
VRBO
#2013 - 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 $306 per night (USD)
VRBO
From $158 per night (USD)
VRBO
Trendy River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $158 per night (USD)
VRBO
From $361 per night (USD)
VRBO
#1512 - 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 $361 per night (USD)
VRBO
From $302 per night (USD)
VRBO
#1115 - 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 $302 per night (USD)
VRBO
From $93 per night (USD)
Expedia
Sleek Loop Studio w/ Pool, Gym & Lounge, near Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this stylish studio Blueground apartment. You’ll love coming home ...
From $93 per night (USD)
Expedia
From $167 per night (USD)
VRBO
Premium South Loop 1BR w/ Gym & Lounge, nr Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this bright one bedroom Blueground apartment. You’ll love coming h ...
From $167 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Ideal Gold Coast 1BR w/ Gym & Lounge, 1 block to L, 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 $185 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Sleek River North 1BR w/ Gym, Lounge & 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 beautiful River North furnished one bedroom a ...
From $214 per night (USD)
VRBO
From $95 per night (USD)
Expedia
Bright Loop 1BR w/ Gym & Doorman, nr L & Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $95 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Sunlit South Loop 1BR w/ Gym & Lounge, nr Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in South Loop with balcony views over the city. It’ll be e ...
From $187 per night (USD)
VRBO
From $547 per night (USD)
Expedia
Captivating Corner PENTHOUSE w/ Lake and Skyline View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A property ideal for the upwardly mobile or traveling elite. This Stylish 2000 square-foot residence is a corner penthou ...
From $547 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Trendy River North 1BR w/ Gym, Lounge & 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 stylish River North furnished one bedroom apa ...
From $161 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Luxe River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, 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 $167 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Modern Streeterville 2BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Streeterville furnished two bed ...
From $150 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Dreamy River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $150 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Sunny River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $137 per night (USD)
VRBO
From $134 per night (USD)
Expedia
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 $134 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Amazing River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, 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 $184 per night (USD)
VRBO
From $627 per night (USD)
VRBO
Corner 3BR in Streeterville | Views | Roof Deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stunning 1,500+ square foot corner apartment with oversize windows, an open layout, and dramatic city and lake ...
From $627 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Bright River North 1BR w/ Gym, Lounge & 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 cozy River North furnished one bedroom apartm ...
From $136 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Amazing Streeterville Jr 1BR w/ Pool & Gym, 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 Streeterville furnished one bedroom ...
From $138 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Roomy Streeterville 2BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Streeterville furnished two bed ...
From $436 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Charming South Loop 1BR w/ Gym & Lounge, nr Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this charming South Loop furnished one bedroom apa ...
From $280 per night (USD)
Expedia
Click For Pricing
VRBO
Chic River North 1BR w/ Gym, Lounge & 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 sophisticated River North furnished one bedro ...
Click For Pricing
VRBO
From $312 per night (USD)
VRBO
Kasa | Fresh & Bright Studio | River North Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $312 per night (USD)
VRBO
Click For Pricing
VRBO
Classic South Loop 1BR w/ Gym & Lounge, nr Grant Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in South Loop. with balcony views over the city. It’ll be ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Trendy Loop 1BR w/ Pool, Gym & Lounge, near 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 Pricing
Expedia
From $659 per night (USD)
VRBO
Breathtaking Downtown Penthouse B - Sleeps 11
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Summary: Absolutely stunning penthouse in a BRAND NEW BUILDING downtown with spectacular city view from your very own pr ...
From $659 per night (USD)
VRBO
Click For Pricing
Expedia
Gorgeous Loop 1BR w/ Gym, Roof Deck, near Millennium Park, 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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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 lovely Chicago Loop furnished one bedroom apa ...
Click For Pricing
VRBO
From $298 per night (USD)
Expedia
Ideal River North 1BR w/ Gym, Lounge & Roof, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $298 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Lovely River North 1BR w/ Gym, Lounge & 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 $227 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Elegant River North 1BR w/ Gym, Lounge & Roof, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Near North with views over the city. It’ll be easy to s ...
From $161 per night (USD)
Expedia
From $159 per night (USD)
VRBO
Amazing Loop Studio w/ Pool & Gym, steps to 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 $159 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Deluxe River North 1BR w/ Gym, Lounge & 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 sophisticated River North furnished one bedro ...
From $162 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Sunlit Streeterville 1BR w/ Pool & Gym, nr Riverwalk, by Blueground
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 $203 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Charming Streeterville 1BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this bright Streeterville furnished one bedroom ap ...
From $358 per night (USD)
Expedia
From $121 per night (USD)
VRBO
Dreamy Streeterville 1BR w/ Pool & Gym, nr Riverwalk, by Blueground
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 $121 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Gorgeous Streeterville 1BR w/ Pool & Gym, nr Riverwalk, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Streeterville furnished one bedroom ...
From $159 per night (USD)
Expedia
From $98 per night (USD)
VRBO
Elegant Loop 1BR w/ Lounge, Gym & Roof Deck, steps to 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 $98 per night (USD)
VRBO
From $886 per night (USD)
Expedia
870 1&2 - 2 Separate Suites in same building
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Summary: You will get 2 separate Suites that are directly next to each other. Each Suite has 2 bedrooms and 2 bathrooms. ...
From $886 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Brownstone, 2 entire units Gold Coast
Bedrooms:
2
Bathrooms:
2
Sleeps:
14
Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...
From $420 per night (USD)
VRBO
From $2650 per night (USD)
Expedia
Downtown Mich Ave - 6 Penthouses, Sleep 25
Bedrooms:
9
Bathrooms:
10
Sleeps:
16
Feel at Home, Unwind, and Enjoy the amenities you deserve at our Michigan Ave Penthouse with 6 combined units! Guests l ...
From $2650 per night (USD)
Expedia
From $270 per night (USD)
VRBO
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living a ...
From $270 per night (USD)
VRBO
From $1251 per night (USD)
Expedia
DTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Feel at Home, Unwind, and Enjoy the amenities you deserve with two 2-Story Downtown Penthouses with Million $ Views. Gu ...
From $1251 per night (USD)
Expedia
From $222 per night (USD)
VRBO
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
"Step into the vibrant heart of River North, where your window frames forever views and the sky blushes with the best s ...
From $222 per night (USD)
VRBO
From $538 per night (USD)
Expedia
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $538 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $570 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Trendy 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 $250 per night (USD)
Expedia
From $488 per night (USD)
VRBO
Chic 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 lovely city and l ...
From $488 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 $294 per night (USD)
VRBO
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $294 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations s ...
From $294 per night (USD)
VRBO
From $132 per night (USD)
VRBO
Charming 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 cozy Chicago Loop furnished one bedroom apart ...
From $132 per night (USD)
VRBO
From $1696 per night (USD)
Expedia
2 Newly Built Luxury Condos with Private Roofdeck!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: This listing is perfect for your Chicago visit! You will get 2 brand new construction units (finished Septembe ...
From $1696 per night (USD)
Expedia
From $170 per night (USD)
VRBO
Brownstone in Gold Coast - Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...
From $170 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Downtown 2BR: Unique Amenities, Ideal for Tourism
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Discover 'The Cooke', a high-end 2BR apartment that's a perfect place for tourism in the heart of Chicago. With ...
From $603 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Best Place to Stay in Chicago! Relaxing Unit w/ City View, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $356 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Discover the Best of Chicago's Loop Near Ford Center Theatre! Pets are Welcome!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Each elegantly designed room at the hotel comes with plush bedding and modern amenities to ensure a comfortable experien ...
From $290 per night (USD)
VRBO
Click For Pricing
VRBO
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 Pricing
VRBO
From $1676 per night (USD)
VRBO
Best Stay! 3 Relaxing Units, Onsite Pool, Parking, Near Art Institute of Chicago
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1676 per night (USD)
VRBO
From $2235 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! 4 Family-friendly Units, Onsite Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $2235 per night (USD)
VRBO
From $1971 per night (USD)
VRBO
Comfort & Convenience, 4 Relaxing Units, Outdoor Swimming Pool, Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1971 per night (USD)
VRBO
From $1676 per night (USD)
VRBO
Great Location! 3 Spacious Units, Outdoor Swimming Pool, Parking Onsite!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1676 per night (USD)
VRBO
From $2235 per night (USD)
VRBO
Relax and Recharge! 4 Comfortable Units, Parking, Onsite Swimming Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $2235 per night (USD)
VRBO
From $994 per night (USD)
VRBO
Comfort & Convenience, 2 Relaxing Units, Outdoor Swimming Pool, Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $994 per night (USD)
VRBO
From $1492 per night (USD)
VRBO
Your Home Away From Home! 3 Relaxing Units, Outdoor Pool, Onsite Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1492 per night (USD)
VRBO
From $994 per night (USD)
VRBO
Best Place to Stay in Chicago! 2 Comfortable Units, Outdoor Pool, Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $994 per night (USD)
VRBO
From $1971 per night (USD)
VRBO
Chicago Gem! 4 Convenient Units, Onsite Pool, Close to Ohio Street Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1971 per night (USD)
VRBO
From $1492 per night (USD)
VRBO
Just What You Were Looking For! 3 Spacious Units, Pool, Close to Navy Pier
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1492 per night (USD)
VRBO
From $1118 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! 2 Family-friendly Units, Onsite Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Just steps from your front door you’ll find an outstanding collection of premium amenities to make you feel more at home ...
From $1118 per night (USD)
VRBO

Search Your Destination Now!

New East Side Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 927 Rentals