Near North Side (Chicago), Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Near North Side (Chicago), Illinois on RentalSaver.com!

Near North Side (Chicago) Rentals

From $233 per night (USD)
VRBO
Two Bedroom West Loop
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Summary: 2 bedroom unit close on the edge of West Loop! The Space: Spacious two bedroom unit that sleeps 7! King Full ( ...
From $233 per night (USD)
VRBO
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
From $193 per night (USD)
Expedia
Blueground | The Loop, pool & gym, nr Willis Tower
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 $193 per night (USD)
Expedia
From $1020 per night (USD)
VRBO
Beautiful Unit CHI in Prime River North - top floor
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: This beautiful unit located on the top floor in downtown is perfect for families, children and corporate gather ...
From $1020 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Panoramic 2BR Penthouse in the Sky | 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 $459 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Luxury Designer Penthouse | Gold Coast/Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own penthouse in Chicago's Gold Coast and Ol ...
From $428 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Chic 2-Bedroom Condo in Gold Coast – Modern & Newl
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the elegance of Chicago’s iconic Gold Coast neighborhood in this newly rehabbed, modern 2-bedroom condo. Thou ...
From $218 per night (USD)
Expedia
From $925 per night (USD)
VRBO
Chic Entire home for Large Groups - Chicago - Bucktown
Bedrooms:
3
Bathrooms:
4
Sleeps:
20
Kick back and relax in this calm, stylish space that features 4 bedrooms, a large basement with bar, fully stocked kitch ...
From $925 per night (USD)
VRBO
From $116 per night (USD)
Expedia
Blueground | River North, pool & gym, nr Mart
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 $116 per night (USD)
Expedia
Click For Pricing
VRBO
Bright, Cozy Apartment by Downtown & Train Stop; Great for Couples/Small Groups
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
No reviews of this unit yet but can see all of my other 5-star reviews here: vrbo/1397667 I have my comfy & cozy apartm ...
Click For Pricing
VRBO
From $892 per night (USD)
VRBO
Four Cozy Queen Rooms! Perfect for Family & Friends, Pets Are Welcome!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $892 per night (USD)
VRBO
From $2695 per night (USD)
VRBO
Ideal Lincoln Park Getaway for Large Groups
Bedrooms:
12
Bathrooms:
16
Sleeps:
32
Summary: Experience unmatched group convenience at 'The Echo' with prime access to Lincoln Park and Chicago's best attra ...
From $2695 per night (USD)
VRBO
From $3657 per night (USD)
VRBO
Gather Your Group: 20BRs in Lincoln Park
Bedrooms:
15
Bathrooms:
20
Sleeps:
40
Summary: Bring your entire crew to 'The Spark,' a unique offering of five 4-bedroom units designed for shared experience ...
From $3657 per night (USD)
VRBO
From $41 per night (USD)
VRBO
The Chicago Hotel Collection, Standard Double Queen with City Views
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 $41 per night (USD)
VRBO
From $113 per night (USD)
Expedia
Blueground | Greektown, bbq, gym, nr Willis Tower
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 $113 per night (USD)
Expedia
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 $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 $249 per night (USD)
VRBO
The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms
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 $124 per night (USD)
VRBO
Sleek Downtown Retreat by Chicago’s Mag Mile @ The Chicago Hotel Collection
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 $124 per night (USD)
VRBO
From $94 per night (USD)
VRBO
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
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 $41 per night (USD)
VRBO
Upscale City Center Stay | Prime Locale | City Views | Pets Allowed
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 $41 per night (USD)
VRBO
From $607 per night (USD)
Expedia
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nestled in the heart of Chicago, this charming apartment boasts 2 cozy bedrooms with queen beds, perfect for a small gro ...
From $607 per night (USD)
Expedia
From $127 per night (USD)
VRBO
Blueground | Near North, pool, nr Millennium Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Near North furnished one bedroom apar ...
From $127 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Blueground | Streeterville, pool, nr Navy Pier
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 $202 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Sun-Drenched 1BR Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to our furnished 1-bedroom apartment—it’s got a nice open layout with large windows that let in tons of ...
From $269 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Urban Comfort • 2BR in West Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Kick back in this stylish 2BR retreat that blends cozy vibes with chic décor and a warm, welcoming living space ...
From $277 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Twice as Nice: Chic 2BR Stay with Style & Space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to your home away from home! This cozy 2BR retreat is all about comfort with a side of style. Located n ...
From $248 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Sleek 1BR Apt w/ Laundry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Comfortable and fully furnished 1BR apartment with all the essentials for a smooth, easy stay. The Space: Our ...
From $269 per night (USD)
Expedia
From $252 per night (USD)
VRBO
The One: A 1BR Stay That Feels Like Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is more than just a place to stay; it’s your cozy, personal retreat. With soft lighting, comfy furnishings ...
From $252 per night (USD)
VRBO
From $769 per night (USD)
VRBO
Entire Home in Lincoln Park - Amazing Game Room - Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This amazing single-family home in the heart of Lincoln Park is steps to popular restaurants and bars, upscale boutiques ...
From $769 per night (USD)
VRBO
From $1002 per night (USD)
VRBO
Spacious Apartments for Groups w/ Skyline Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Summary: 'The Tribune' is ideal for family and friends visiting West Loop’s best. Our first group of 2025 left a perfe ...
From $1002 per night (USD)
VRBO
From $441 per night (USD)
Expedia
River North | Rooftop With In & Out Parking | 3
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, two ...
From $441 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Brand-New West Loop 3BR + City Views for Families
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience brand-new luxury at 'The Lyric,' a stunning 3BR in in West Loop’s vibrant Fulton District. You're ...
From $452 per night (USD)
VRBO
From $84 per night (USD)
Expedia
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)
Expedia
From $220 per night (USD)
VRBO
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)
VRBO
From $303 per night (USD)
Expedia
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)
Expedia
From $542 per night (USD)
VRBO
South Loop | Rooftop With In & Out Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bat ...
From $542 per night (USD)
VRBO
From $316 per night (USD)
Expedia
River North | Rooftop With In & Out Parking | 1
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $316 per night (USD)
Expedia
From $439 per night (USD)
VRBO
South Loop | Rooftop With In & Out Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bat ...
From $439 per night (USD)
VRBO
From $410 per night (USD)
Expedia
River North | Rooftop With In & Out Parking | 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, two ...
From $410 per night (USD)
Expedia
From $360 per night (USD)
VRBO
River North | Private Balcony With In&Out Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $360 per night (USD)
VRBO
From $351 per night (USD)
Expedia
River North | Rooftop With In & Out Parking | 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Enjoy a stylish experience at this centrally-located place. Stunning 1,000 square foot modern two bedroom, one ...
From $351 per night (USD)
Expedia
From $687 per night (USD)
VRBO
River North Private Deck With In and Out Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, on ...
From $687 per night (USD)
VRBO
From $967 per night (USD)
Expedia
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Chicago getaway! This stunning, newly rehabbed classic red brick Victorian home offers a blend o ...
From $967 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Wicker Park - Loft Style Home in Lively Location with Plenty Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the ultimate relaxation in our Wicker Park apartment, designed for fun and comfort. Enjoy amenities like a po ...
From $189 per night (USD)
VRBO
From $135 per night (USD)
VRBO
Short Drive to Millennium Park & Willis Tower with Rooftop Lounge
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 $135 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Dip into Heated Pool & Relax in 2 Modern Rooms | Walk to Chicago Riverwalk
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 $289 per night (USD)
VRBO
From $289 per night (USD)
VRBO
2 Boutique-Style Rooms | Indoor Pool, Gym, & Near Magnificent Mile
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 $289 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Stay Cool w/ Rooftop Deck & Fitness Room Near Chicago Riverwalk
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 $136 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Rooftop Relaxation w/ Pool + Gym | Walk to Millennium Park and Chicago Riverwalk
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 $144 per night (USD)
VRBO
From $144 per night (USD)
VRBO
Stay in Heart of Chicago | Rooftop Deck, Gym and Near Millennium Park
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 $144 per night (USD)
VRBO
From $191 per night (USD)
VRBO
La Quinta – Deluxe King Room with City Views in Chicago Loop
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Surrounded by iconic architecture and vibrant dining, La Quinta Chicago offers city access and skyline views in the Loop ...
From $191 per night (USD)
VRBO
From $189 per night (USD)
VRBO
La Quinta – King Suite with Living Area Near Chicago Landmarks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just off Wacker Drive, La Quinta provides easy access to Union Station and the Magnificent Mile. This non-smoking king s ...
From $189 per night (USD)
VRBO
From $91 per night (USD)
Expedia
Blueground | Streeterville, rooftop pool, nr Navy Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this studio apartment in Streeterville. It’ll be easy to simply show up and start liv ...
From $91 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Fully Furnished Gold Coast Luxury Condo with Sunset View Ideal for 30+ Day Stays
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Luxury High-Rise Condo in Chicago’s Gold Coast, Perfect for Long-Term Stays Experience upscale city living in this full ...
From $130 per night (USD)
VRBO
From $549 per night (USD)
Expedia
Designer Apartment 2W | Heart of Gold Coast/River North
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Chica ...
From $549 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Secret Gallery on the Park - 2bd/1ba + 1bd/1ba
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $368 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Sophisticated 4BR Suite - Modern, and Luxurious
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $460 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Corporate-Friendly 4BR Stylish & Central
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $461 per night (USD)
VRBO
From $390 per night (USD)
Expedia
3BR City Escape Bright, Sleek, Spacious
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 3- Bedroom is meticulously designe ...
From $390 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Modern 4BR City Retreat with Stunning Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 4-Bedroom is meticulously designed ...
From $461 per night (USD)
VRBO
From $464 per night (USD)
Expedia
4BR Modern Gem Sleek, Bright & Central
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 4-Bedroom is meticulously designed ...
From $464 per night (USD)
Expedia
From $463 per night (USD)
VRBO
Chic 4-Bedroom with Skyline Views & Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 4- Bedroom is meticulously designe ...
From $463 per night (USD)
VRBO
From $299 per night (USD)
Expedia
2BR City Escape Bright, Sleek, Spacious
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury suite is meticulously designed for ...
From $299 per night (USD)
Expedia
From $460 per night (USD)
VRBO
4BR Corporate Suite Central and Modern
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $460 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Family-Sized 4BR Luxury in Downtown Chicago
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 4-Bedroom is meticulously designed ...
From $461 per night (USD)
Expedia
From $471 per night (USD)
VRBO
Brand New 4BR in Heart of Chicago
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $471 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Group-Ready 3BR Sleek Design & Great Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 3- Bedroom is meticulously designe ...
From $395 per night (USD)
Expedia
From $459 per night (USD)
VRBO
High-Rise 4BR w Views, Comfort & Space
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury 4- Bedroom is meticulously designe ...
From $459 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Elegant 3BR Stay Prime Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury place is meticulously designed for ...
From $394 per night (USD)
Expedia
From $579 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 $579 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
From $125 per night (USD)
VRBO
Blueground | Goose Island, view, nr Lincoln Park
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 $125 per night (USD)
VRBO
From $260 per night (USD)
Expedia
West Loop Living – Bright 1BR
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to your stylish city escape in one of Chicago’s most vibrant and walkable neighborhoods — the West Loop ...
From $260 per night (USD)
Expedia
From $692 per night (USD)
VRBO
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)
VRBO
From $111 per night (USD)
Expedia
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)
Expedia
From $343 per night (USD)
VRBO
Sunny & Spacious Bucktown 3Bd/2Ba w/Laundry
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful Condo Quality Fully Furnished and Renovated space for monthly rental. A super spacious 3 bedroom, 2 bath apa ...
From $343 per night (USD)
VRBO
From $317 per night (USD)
VRBO
2 Spacious Rooms with 2 Queen Beds Near Magnificent Mile
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
With walkable access to shopping, theaters, and public transport, La Quinta Downtown is ideal for family visits or frien ...
From $317 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Blueground | West Town, washer, nr Chicago River
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 $134 per night (USD)
VRBO
From $81 per night (USD)
Expedia
Blueground | West Town, pets allowed, nr Park
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 $81 per night (USD)
Expedia
From $139 per night (USD)
VRBO
Blueground | Rush & Division, balcony, nr Lake Shore Park
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 $139 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 $235 per night (USD)
VRBO
City Studio Escape Bright, Sleek & Modern
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury space is meticulously designed for ...
From $235 per night (USD)
VRBO
From $278 per night (USD)
Expedia
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)
Expedia
From $249 per night (USD)
VRBO
Chicago Citrus Charm 2BR WestTown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step into this vibrant and stylish two bedroom apartment, perfectly located just minutes from downtown Chicago! Designed ...
From $249 per night (USD)
VRBO
From $125 per night (USD)
VRBO
Downtown Living: Walkable, Modern Chicago Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Remote Work Ready | Willis Tower View | On-Site Market Stay in the Loop — where every meeting, meal, and museum is just ...
From $125 per night (USD)
VRBO
From $565 per night (USD)
VRBO
Chicago Townhome with Roof Deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the best of Chicago in this beautifully designed 3-bedroom, 3-bath townhouse in the vibrant West Town neighbo ...
From $565 per night (USD)
VRBO
From $559 per night (USD)
Expedia
NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Immerse yourself in this stylish 3 bed, 2.5 bath luxury townhouse in Chicago's vibrant West Loop. You're steps away fro ...
From $559 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Chicago's Leafy Street Hideaway - 1 Bedroom Condo with a Side of Sass
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vintage charm meets modern upgrades in this remodeled 1BR apartment. High ceilings, original hardwoods, and a kitchen wi ...
From $125 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Flexhome West Town 2BR Apt T1
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The space: The apartment comfortably sleeps 4 and has flexible seating areas so you can work or relax at your convenienc ...
From $180 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Archways at the Lincoln Park Zoo 2bed/2ba
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history ...
From $250 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Flexhome West Town 2BR Apt T1
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The space: The apartment comfortably sleeps 4 and has flexible seating areas so you can work or relax at your convenienc ...
From $597 per night (USD)
Expedia
From $138 per night (USD)
VRBO
Pet Friendly Queen Unit! Near Chicago Attractions!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a great location in a trendy neighborhood near shopping, dining, and attractions, this is the perfect spot for your ...
From $138 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Modern Queen Stay! Pet Friendly Accommodation w/ Gym Access | Chicago Riverwalk!
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 $175 per night (USD)
VRBO

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