Chicago Harbor Rentals
From $237 per night (USD)VRBO
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)VRBO
From $103 per night (USD)Expedia
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)Expedia
From $99 per night (USD)VRBO
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)VRBO
From $138 per night (USD)Expedia
Hip River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Rush & Division furnished one bedroom ap ...
From $138 per night (USD)Expedia
From $181 per night (USD)VRBO
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, 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 $181 per night (USD)VRBO
From $233 per night (USD)Expedia
Beautiful Streeterville 1BR w/ Deck & Pool, walk to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Streeterville furnished one bedroom apa ...
From $233 per night (USD)Expedia
From $129 per night (USD)VRBO
Sleek Streeterville Studio w/ Pool & Gym, near Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this comfortable studio Blueground apartment. You’ll love coming h ...
From $129 per night (USD)VRBO
From $842 per night (USD)Expedia
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)Expedia
From $91 per night (USD)VRBO
Splendid Loop Studio w/ Gym, Doorman, walk to L & Parks, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming studio Blueground apartment. You’ll love coming home ...
From $91 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 $1841 per night (USD)Expedia
Old-World, Classic Building Downtown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Our beautiful Brownstone Apartment is located in the heart of bustling GOLD COAST on a street shared with homes ...
From $1841 per night (USD)Expedia
From $175 per night (USD)VRBO
Luxe Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Streeterville with high floor views over the lake. It’l ...
From $175 per night (USD)VRBO
From $85 per night (USD)Expedia
Bright South Loop Studio w/ Pool, Gym, walk to Grant Park, by Blueground (ID #CHI347)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Central Station with high floor views over the city. It’ll b ...
From $85 per night (USD)Expedia
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)Expedia
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)Expedia
From $105 per night (USD)VRBO
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, 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 $105 per night (USD)VRBO
From $114 per night (USD)Expedia
Open River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with high floor views over the city. It ...
From $114 per night (USD)Expedia
From $169 per night (USD)VRBO
Roomy River North 2BR w/ Gym, Deck & Pool, walk to Mag Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Rush & Division furnished two bedroom ...
From $169 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 $153 per night (USD)VRBO
Ideal Streeterville Studio w/ Gym, Pool, walk to Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in Streeterville with high floor views over the city. It’ll be ...
From $153 per night (USD)VRBO
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 $147 per night (USD)VRBO
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 $147 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 $96 per night (USD)VRBO
Fantastic River North 1BR w/ Gym, Rooftop, 1 block to L, 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 $96 per night (USD)VRBO
From $1181 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 $1181 per night (USD)Expedia
From $580 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 $580 per night (USD)VRBO
From $137 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 $137 per night (USD)VRBO
From $148 per night (USD)VRBO
Modern South Loop 1BR w/ Pool + Gym, walk to Soldier Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Central Station furnished one bedroom ...
From $148 per night (USD)VRBO
From $170 per night (USD)Expedia
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)Expedia
From $4175 per night (USD)VRBO
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)VRBO
From $156 per night (USD)Expedia
Charming River North 1BR w/ Gym, Pool, near L stop & Beach, 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 $156 per night (USD)Expedia
From $169 per night (USD)VRBO
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Apartment with kitchen, steps from State Street Concierge services and free WiFi in public areas are available at this s ...
From $169 per night (USD)VRBO
From $269 per night (USD)Expedia
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 $269 per night (USD)Expedia
From $777 per night (USD)VRBO
Historic luxury townhouse on Chicago's Gold Coast
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after loca ...
From $777 per night (USD)VRBO
From $599 per night (USD)Expedia
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)Expedia
From $120 per night (USD)VRBO
Tasteful Streeterville 1BR w/ Gym, Pool, near 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 $120 per night (USD)VRBO
From $135 per night (USD)Expedia
Elegant Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty studio Blueground apartment. You’ll love coming home t ...
From $135 per night (USD)Expedia
From $324 per night (USD)VRBO
Modern 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 $324 per night (USD)VRBO
From $888 per night (USD)Expedia
55-56 Mag Mile Penthouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: The Penthouses at Grand Plaza PH#1 A stunning rental 55 stories above Chicago. With dramatic living spaces, a c ...
From $888 per night (USD)Expedia
From $311 per night (USD)VRBO
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)VRBO
From $313 per night (USD)Expedia
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)Expedia
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 $855 per night (USD)Expedia
Lovely 4 Bedroom Spot located in Charming Old Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Huge, 2500 sqft Condo in Chicago's most Exciting, Safe, and Historic Neighborhood: Old Town. This is a Private, Full Flo ...
From $855 per night (USD)Expedia
From $303 per night (USD)VRBO
Stunning 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 $303 per night (USD)VRBO
From $93 per night (USD)Expedia
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)Expedia
From $292 per night (USD)VRBO
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)VRBO
From $393 per night (USD)Expedia
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)Expedia
From $178 per night (USD)VRBO
Splendid Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground
- 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 $178 per night (USD)VRBO
From $92 per night (USD)Expedia
Lovely Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Streeterville furnished one bed ...
From $92 per night (USD)Expedia
From $306 per night (USD)VRBO
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)VRBO
From $309 per night (USD)Expedia
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)Expedia
From $297 per night (USD)VRBO
Downtown MICH AVE#4 King Beds |Grant Park, 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $297 per night (USD)VRBO
From $165 per night (USD)Expedia
Quaint River North 1BR w/ Gym + W/D near Mag Mile by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with high floor views over the city. It ...
From $165 per night (USD)Expedia
From $174 per night (USD)VRBO
Ideal River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- 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 $174 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
Click For PricingVRBO
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 PricingVRBO
From $290 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 $290 per night (USD)VRBO
From $137 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 $137 per night (USD)VRBO
From $137 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 $137 per night (USD)VRBO
From $434 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 $434 per night (USD)VRBO
From $76 per night (USD)Expedia
Modern Gold Coast Studio w/ Doorman & Gym, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious studio Blueground apartment. You’ll love coming home ...
From $76 per night (USD)Expedia
From $146 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 $146 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $241 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 $241 per night (USD)VRBO
From $173 per night (USD)Expedia
Airy Gold Coast 2BR w/ Gym, Pool, near. Oak St. Beach, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Rush & Division furnished two bedroom ...
From $173 per night (USD)Expedia
From $242 per night (USD)VRBO
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)VRBO
From $233 per night (USD)Expedia
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 $233 per night (USD)Expedia
From $202 per night (USD)VRBO
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)VRBO
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 $403 per night (USD)VRBO
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 $403 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
From $119 per night (USD)VRBO
Amazing Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, 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 $119 per night (USD)VRBO
From $175 per night (USD)Expedia
Dreamy South Loop Studio w/ Pool, Gym, Roof Deck, near L, by Blueground (#CHI430)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy studio Blueground apartment. You’ll love coming home to ...
From $175 per night (USD)Expedia
From $222 per night (USD)VRBO
2/2 Apt in the City | Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad (*NO PARTIES*) to explore the heart o ...
From $222 per night (USD)VRBO
From $103 per night (USD)Expedia
Airy South Loop Studio w/ Pool, Gym & Spa, nr Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Central Station with high floor views over the city. It ...
From $103 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 $139 per night (USD)Expedia
Spacious South Loop Studio w/ Gym, 1 block from CTA Train, by Blueground (ID #CHI348)
- 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 $139 per night (USD)Expedia
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 $193 per night (USD)Expedia
Charming South Loop 2BR w/ Pool, Gym & Spa, nr Grant Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Central Station with views over the city. It’ll be easy ...
From $193 per night (USD)Expedia
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 $90 per night (USD)Expedia
Hip Gold Coast Studio 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 $90 per night (USD)Expedia
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)Expedia
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)Expedia
From $1187 per night (USD)VRBO
Downtown Sleep 20 | Mag Mile 6bd/6ba
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐚𝐭 𝐨𝐮𝐫 𝐪𝐮 ...
From $1187 per night (USD)VRBO
From $134 per night (USD)Expedia
Mod South Loop 1BR w/ Lounge, Pool & Gym near Grant 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 $134 per night (USD)Expedia
From $168 per night (USD)VRBO
Hip South Loop Studio w/ Lounge, Pool & Gym near Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this studio apartment in South Loop with views over the city. It’ll be easy to simply ...
From $168 per night (USD)VRBO
From $125 per night (USD)Expedia
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 ...
From $125 per night (USD)Expedia
From $119 per night (USD)VRBO
Premium South Loop 2BR w/ Gym & Roof, nr Grant Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...
From $119 per night (USD)VRBO
From $412 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 $412 per night (USD)VRBO
From $156 per night (USD)VRBO
Dreamy South Loop Studio w/ Pool, BBQ & Gym, nr Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming studio Blueground apartment. You’ll love coming home ...
From $156 per night (USD)VRBO
From $109 per night (USD)Expedia
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 $109 per night (USD)Expedia
From $569 per night (USD)VRBO
5-Star Gold Coast Experience in a Luxe 2BR Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Experience the best of Chicago in 'The Wicked,' a premium 2BR retreat offering panoramic skyline views. With 10 ...
From $569 per night (USD)VRBO
From $515 per night (USD)Expedia
2BR Retreat in Downtown + City Skyline Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Ideal for tourists seeking spacious luxury in 'The Hamilton,' steps from Michigan Avenue. With 88% 5-star revie ...
From $515 per night (USD)Expedia