Chicago Harbor Rentals
From $211 per night (USD)VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $211 per night (USD)VRBO
From $552 per night (USD)VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $552 per night (USD)VRBO
From $298 per night (USD)VRBO
Stylish Streeterville 2BR w/ Lounge & Pool, nr Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $298 per night (USD)VRBO
From $215 per night (USD)Expedia
Upscale Streeterville Jr 1BR w/ Gym, nr Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $215 per night (USD)Expedia
From $103 per night (USD)VRBO
Trendy Loop Jr 1BR w/ Game Room, nr Park & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Chicago Loop furnished one bedroom apa ...
From $103 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 $292 per night (USD)VRBO
Downtown 2bd #4 - Near Grant Park, Museums, Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $292 per night (USD)VRBO
From $96 per night (USD)Expedia
Blueground | South Loop 1bd apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $96 per night (USD)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 $1520 per night (USD)Expedia
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)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 $668 per night (USD)Expedia
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $668 per night (USD)Expedia
From $370 per night (USD)VRBO
Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $370 per night (USD)VRBO
From $161 per night (USD)VRBO
Better Choice for your Vacation! Short Walk to River North Spots, Pets Allowed!
- 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 $161 per night (USD)VRBO
From $143 per night (USD)VRBO
Everything You Need For The Perfect Vacation! Pet-friendly Property, King Room!
- 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 $143 per night (USD)VRBO
From $253 per night (USD)Expedia
Blueground | South 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 cozy South Loop furnished one bedroom apartme ...
From $253 per night (USD)Expedia
From $249 per night (USD)VRBO
Blueground | South Loop, pool & gym, nr park
- 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 $249 per night (USD)VRBO
From $228 per night (USD)VRBO
Suite Success • Business Class Living • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your extended-stay retreat in the heart of Chicago’s South Loop. Whether you’re here for work, relocating to ...
From $228 per night (USD)VRBO
From $84 per night (USD)VRBO
Blueground | Rush & Division, fitness center, nr Lincoln Park
- 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 $84 per night (USD)VRBO
From $220 per night (USD)Expedia
Luxury Unit with Rooftop Lounge & Spectacular City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 248 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $220 per night (USD)Expedia
From $303 per night (USD)VRBO
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 301 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $303 per night (USD)VRBO
From $340 per night (USD)Expedia
Bright 3BR Retreat Near McCormick + Museum Campus
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 1-bath apartment perfect for everyone! Just minutes ...
From $340 per night (USD)Expedia
From $719 per night (USD)VRBO
Spectacular Gold Coast Villa Near Beach w/ Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to the Gold Coast Villa Retreat — a stunning, fully renovated private home designed for families, groups, and bu ...
From $719 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 $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 $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 $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 $346 per night (USD)VRBO
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city ...
From $346 per night (USD)VRBO
From $200 per night (USD)VRBO
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 $200 per night (USD)VRBO
From $202 per night (USD)Expedia
Premium Gold Coast 1BR w/ Doorman & Gym, 2 blocks 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 Gold Coast furnished one bedroom ap ...
From $202 per night (USD)Expedia
From $532 per night (USD)VRBO
Stunning 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $532 per night (USD)VRBO
From $599 per night (USD)VRBO
Modern 3BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $599 per night (USD)VRBO
Click For PricingVRBO
DOWNTOWN STUDIO BY RUSH STREET -GOLD COAST CENTER
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 60
Gold Coast is Downtown Chicago’s best neighborhood to be! This is an “Entire Space” private studio (Hotel size) only for ...
Click For PricingVRBO
From $242 per night (USD)Expedia
Smart Loop 1BR w/ Gym, Pool, W/D, nr. Millennium Park, 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 $242 per night (USD)Expedia
From $331 per night (USD)VRBO
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $331 per night (USD)VRBO
From $954 per night (USD)VRBO
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $954 per night (USD)VRBO
From $483 per night (USD)VRBO
Stylish Corner 2 Bedroom in the Heart of Chicago | 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 $483 per night (USD)VRBO
From $477 per night (USD)VRBO
Fabulous Corner 2 Bedroom 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 $477 per night (USD)VRBO
From $269 per night (USD)VRBO
Generous River North 3BR w/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI324)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the best of Chicago, with this three bedroom apartment in River North with balcony views over the city. It’ll b ...
From $269 per night (USD)VRBO
From $237 per night (USD)Expedia
Downtown Guild #4 | Mag Mile, Gold Coast, The Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $237 per night (USD)Expedia
From $103 per night (USD)VRBO
Mod Loop 1BR, w/ Gym, Pool nr the Millenium Park 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 $99 per night (USD)Expedia
Ideal River North 1BR w/pool, gym, nr. L & Magnificent Mile
- 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 $99 per night (USD)Expedia
From $842 per night (USD)VRBO
Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
🛏 Sleeping Arrangements, Plenty of room for everyone to have their own space! Bedroom 1: King bed Bedroom 2: Queen bed ...
From $842 per night (USD)VRBO
From $388 per night (USD)VRBO
Stunning 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 city an ...
From $388 per night (USD)VRBO
From $522 per night (USD)VRBO
Spectacular Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $522 per night (USD)VRBO
From $2796 per night (USD)Expedia
The Orleans - Entire Building - With Rooftop Deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $2796 per night (USD)Expedia
From $214 per night (USD)VRBO
LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streetervil ...
From $214 per night (USD)VRBO
From $567 per night (USD)VRBO
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfec ...
From $567 per night (USD)VRBO
From $167 per night (USD)VRBO
Mod River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Rush & Division with high floor views over the city. It ...
From $167 per night (USD)VRBO
From $211 per night (USD)Expedia
Ideal Gold Coast 2BR, w/ Gym, Lounge, W/D, nr Oak Street by Blueground
- 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 $211 per night (USD)Expedia
From $446 per night (USD)VRBO
Beautiful Corner 2 Bedroom 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 $446 per night (USD)VRBO
From $755 per night (USD)Expedia
MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome! You've found a hidden gem in the Gold Coast / Streeterville neighborhood: Guests love our home because: - You ...
From $755 per night (USD)Expedia
From $639 per night (USD)VRBO
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertai ...
From $639 per night (USD)VRBO
From $233 per night (USD)Expedia
Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
51st Floor! Best Value in Chicago! Luxe condo in a FANTASTIC location! Perfect for vacation, short-term housing or cor ...
From $233 per night (USD)Expedia
From $170 per night (USD)VRBO
Smart River North 1BR w/ Gym, Pool, near L stop & Beach, 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 $170 per night (USD)VRBO
From $4175 per night (USD)Expedia
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Chicago’s Gold Coast Luxury Single Family Home. The location is so perfect it cannot be beat! IG: ChicagoLuxuryVRBO. We ...
From $4175 per night (USD)Expedia
From $599 per night (USD)VRBO
53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: The Penthouses at Grand Plaza PH#3 This stunning two-story Penthouse soars above Chicago, featuring dramatic li ...
From $599 per night (USD)VRBO
From $311 per night (USD)Expedia
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#5 Experience elevated city living from this stunning penthouse, soaring 52 sto ...
From $311 per night (USD)Expedia
From $313 per night (USD)VRBO
53 Floor MagMile Penthouse Views, Balcony, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Penthouses at Grand Plaza PH#6 This 2-bedroom/2-bath soars 53 floors above Chicago, featuring dramatic livi ...
From $313 per night (USD)VRBO
From $463 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 $463 per night (USD)VRBO
From $93 per night (USD)VRBO
Airy River North 1BR w/ Gym, Pool, near L stop & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable Near North furnished one bedroom ...
From $93 per night (USD)VRBO
From $292 per night (USD)Expedia
Safe Downtown Penthouse #1 | Vintage 2bd (+Gym)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to MillenniumPark, Sk ...
From $292 per night (USD)Expedia
From $393 per night (USD)VRBO
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy a Spacious, Homey 3bd Penthouse (+Patio) with your Family & Friends near Grant Park! We are a short walk to Mille ...
From $393 per night (USD)VRBO
From $306 per night (USD)Expedia
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $306 per night (USD)Expedia
From $309 per night (USD)VRBO
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $309 per night (USD)VRBO
From $269 per night (USD)Expedia
Amazing Gold Coast 2BR w/ Gym & Lounge, 1 block from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Rush & Division furnished two bedroom ...
From $269 per night (USD)Expedia
From $291 per night (USD)VRBO
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)VRBO
From $410 per night (USD)Expedia
Downtown 3bd #7 near Park+Museums
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $410 per night (USD)Expedia
From $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 $90 per night (USD)Expedia
Luxe River North 1BR w/ Pool & Fitness Area, 1 Block to L, 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 $90 per night (USD)Expedia
From $485 per night (USD)VRBO
Downtown Penthouse Lake Views #1|Gym, Parking+Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Feel at Home, Unwind, and Enjoy the amenities you deserve at our 2-Story Penthouse with Million $ Views. Guests love st ...
From $485 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
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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 PricingVRBO
From $141 per night (USD)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 sophisticated Near North furnished one bedroo ...
From $141 per night (USD)Expedia
From $114 per night (USD)VRBO
Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $114 per night (USD)VRBO
From $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 $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 $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 $1173 per night (USD)Expedia
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)Expedia
From $132 per night (USD)VRBO
Blueground | South Loop 1bd apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $132 per night (USD)VRBO
From $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 $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 $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
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City View Smart, luxurious 1bd apartment - Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
City View Smart, luxurious 1BD apartment with stunning Chicago skyline views, a personalized Pilates reformer, and centr ...
Click For PricingExpedia
From $286 per night (USD)VRBO
2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Modern 2-bedroom apartment in Chicago’s peaceful South Loop. Located across from McCormick Place and Wintrust Stadium, ...
From $286 per night (USD)VRBO
From $692 per night (USD)Expedia
Elevated 2BR Retreat + Balcony with Bean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience luxury in 'The Luma,' a prime 2BR in the Loop with breathtaking views, perfect for city explorers. W ...
From $692 per night (USD)Expedia
From $111 per night (USD)VRBO
Luxury 1BR Condo – Views, Comfort, & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your home away from home—an upscale, sun-filled 1-bedroom condo located on the 41st floor in the heart of Chi ...
From $111 per night (USD)VRBO
From $768 per night (USD)Expedia
Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your perfect Chicago getaway at 111 W Elm St — where classic elegance meets modern comfort in the heart of th ...
From $768 per night (USD)Expedia
From $278 per night (USD)VRBO
Boulevard Stays | 5 Minutes to Magnificent Mile and River North
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience chic comfort in this modern River North retreat—just 5 minutes from the Magnificent Mile, CTA, top d ...
From $278 per night (USD)VRBO
From $296 per night (USD)Expedia
Stylish 2BR Cozy South Loop Suite Near McCormick
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your chic and cozy home in the heart of Chicago’s vibrant South Loop! Just steps away from McCormick Place, t ...
From $296 per night (USD)Expedia
From $298 per night (USD)VRBO
Charming 2BR Unit Near McCormick & Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your stylish urban retreat in the heart of Chicago's vibrant South Loop! This spacious and fully-equipped 2-b ...
From $298 per night (USD)VRBO
From $290 per night (USD)VRBO
2 Spacious Units Close to Navy Pier! Pool, Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $290 per night (USD)VRBO
From $436 per night (USD)VRBO
Your Chicago Adventure Starts Here! 3 Units! Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $436 per night (USD)VRBO
From $146 per night (USD)VRBO
Large Unit Close to the Millennium Park! Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaur ...
From $146 per night (USD)VRBO