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Chicago Rentals

From $283 per night (USD)
VRBO
2-bedroom apartment just 2 minutes drive to Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $283 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Wrigleyville Suites Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $324 per night (USD)
Expedia
From $486 per night (USD)
VRBO
3BR Luxury Modern Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most ...
From $486 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Cozy apartment near zoo, DePaul, Oz Park and much more!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $278 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Cozy & Colorful garden unit in Logan Square
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Escape to our private 3 bedroom garden condo in trendy Logan Square. This urban retreat offers a cozy living space with ...
From $204 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Beautiful Apartment in Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
16
Great apartment in ChicagoWhat will guests love about your area? Ghost tours, a buzzing restaurant district, or a night ...
From $167 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Penthouse Loft in Chicago. As avid travelers and frequent VRBO users, we've infused our home with inspira ...
From $231 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Charming 2-bedroom apartment in hip Chicago
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Chicago at this delightful apartment. With 2 bedrooms, including a king bed and a queen bed, this property is ...
From $235 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Family, Groups - Convenient to Wrigley, Loop, Airport - Spacious 2200 Sq Ft
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $392 per night (USD)
VRBO
From $696 per night (USD)
Expedia
6BR Chicago Gem: Prime, Safe, Family-Friendly Hub
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Experience Chicago in an unmatched setting: two apartments beautifully united into a grand 6-bedroom, 2-bathroom home in ...
From $696 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
Bedrooms:
2
Bathrooms:
5
Sleeps:
18
Gorgeous gem within 10 miles of Downtown, Airport, Lake Michigan, and United Center! About 15 miles from Wrigley Field ...
From $570 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Modern Condo • Safe Chicago Stay Near O’Hare
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
✨ Place was clean and comfortable. Easily accessible to airport, gym, grocery stores, etc. I felt safe in the area. ✨ ...
From $302 per night (USD)
Expedia
From $714 per night (USD)
VRBO
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
✨ I highly recommend this location. The home is beautiful and quaint. The location is perfect. The neighbor is very quie ...
From $714 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Home Away From Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our charming Chicago rental home, " A Home Away From Home"! This vacation retreat offers a serene ambiance th ...
From $353 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Updated 3 Bedroom Chicago Historic Andersonville
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $322 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Suite 2 on Southport 4 Queen Beds
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $205 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
A spacious updated bungalow at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Nei ...
From $234 per night (USD)
VRBO
$Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \CASA PILSEN\$
From $72 per night (USD)
Expedia
Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \"CASA PILSEN\"
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Casa Pilsen!! Located in the heart of Pilsen, enjoy what this 1-bedroom apartment has to offer. This fabulous ...
From $72 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Unwind in the stylish two-bedroom apt on Beach Street, a street in Chicago. The city is full of award-winning restaurant ...
From $284 per night (USD)
VRBO
From $266 per night (USD)
Expedia
The Banksy-Greystone Rooftop Firepit United Center
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Banksy, this modern apartment offers 2 bedrooms, one with a king bed and a queen bed. The apartment also features a ...
From $266 per night (USD)
Expedia
From $184 per night (USD)
VRBO
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the charm and convenience of our unique tiny apartment in La Vecindad, perfect for your stay in Pilsen, Chica ...
From $184 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Charming Pilsen Studio - Quick Access to Downtown Chicago!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover the charm of our unique studio apartment in La Vecindad, your perfect retreat in Pilsen, Chicago! This cozy stu ...
From $184 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This memorable apartment is the perfect home base for your trip to Chicago. With 3 bedrooms, including 1 king bed, 1 que ...
From $383 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Chicago Cityview Chic II Gold Coast/River North
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our stylish, 2-bed, 2-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover the epi ...
From $269 per night (USD)
Expedia
From $666 per night (USD)
VRBO
Family-Friendly South Loop Escape by RedAwning
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
If you're seeking urban living, this 3 1/2-story unit is for you. A spacious townhome, it's ideally nestled between McC ...
From $666 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Quick Drive to Downtown Chicago & Early Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Book your stay now at our modern, fully furnished condo—just minutes from downtown Chicago and the Illinois Medical Dist ...
From $240 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Near O`hare • Personal Gym & Balcony • Safe Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
✨ Much cheaper than a hotel, and definitely bigger and more comfortable than the four star hotels on the other side of t ...
From $146 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Neat Old Town 1BR Gym, W/D, Rooftop, BBQ & A/C, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Old Town furnished one bedroom ...
From $144 per night (USD)
Expedia
From $115 per night (USD)
VRBO
1-bedroom condo next to Chicago Midway International Airport
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your Chicago adventure begins at this delightful 1-bedroom condo. The cozy bedroom features a queen bed, while the bathr ...
From $115 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The apartment is exclusively yours, without interruption for the duration of your stay, so relax, unwind, and make yours ...
From $225 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Chic 1-bedroom apartment in phenomenal Chicago with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover the beauty of Chicago from this enchanting 1-bedroom apartment. With a cozy living room featuring a futon, gues ...
From $201 per night (USD)
VRBO
From $215 per night (USD)
Expedia
NEW modern 2BR apt near UofChicago & Hyde Park w/free Parking & pet-friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sleek, secure, and sun-drenched! This brand-new 2-bedroom, 1-bath garden unit is your tech-savvy urban oasis with a priv ...
From $215 per night (USD)
Expedia
From $946 per night (USD)
VRBO
Wrigleyville 3BD Condo
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $946 per night (USD)
VRBO
From $1025 per night (USD)
VRBO
Wrigleyville Garden 3BR/9beds Pod
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1025 per night (USD)
VRBO
From $185 per night (USD)
VRBO
Relaxing Chicago Vibe - Minutes away from major attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated condo, perfect for up to 4 guests. This spotless space is meticulously cleaned and maintained to ensure ...
From $185 per night (USD)
VRBO
From $243 per night (USD)
VRBO
2 Bed & 3 Bath Chicago Condo
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: Kick back and relax in this calm, stylish space minutes away from Chicago's best attractions. Step inside thi ...
From $243 per night (USD)
VRBO
From $479 per night (USD)
VRBO
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience luxurious living in Chicago! This brand new, spacious 2-bedroom 2-bath penthouse apartment offers an ...
From $479 per night (USD)
VRBO
From $123 per night (USD)
VRBO
Cozy 2BR Self-checkin unit in Chicago l Few Steps from DT I Car Rental Available
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located within just 8 miles from Downtown Chicago, enjoy what this 2-bedroom apartment has to offer. INBOX ME FOR ON-SIT ...
From $123 per night (USD)
VRBO
From $189 per night (USD)
VRBO
Three Bed Spacious Comfy Apt by Midway Airport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Discover the perfect balance of comfort and convenience in this beautifully renovated 3-bedroom, 2-bath apartme ...
From $189 per night (USD)
VRBO
From $400 per night (USD)
VRBO
Chic 2-bedroom condo in amazing Chicago minutes from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Kick back and relax in this calm, stylish space in the heart of Chicago’s legendary Bronzeville neighborhood. This styl ...
From $400 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Pine Beam Sloth Apartment next to Blue Line
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our charming 650 sq ft, 1-bedroom apartment! It's the perfect size for comfortable living, offering a well-e ...
From $276 per night (USD)
VRBO
From $803 per night (USD)
Expedia
Rainbow Guest House: Charming 3-bedroom house in great location
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Your Chicago adventure begins at this 3-bedroom house. Welcome to Rainbow Guest House. This designer owned, rebuilt and ...
From $803 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Spacious, one-level condo next to Jackson Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this condo in picturesque Chicago. This beautiful rental features 3 queen beds spread across 3 bedrooms, ensur ...
From $333 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Minutes from O`Hare | Safe Neighborhood | Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
✨ “ Super comfy couch (one of my favorites and we have been traveling in airbnbs for 6 months)” ✨ 👉 Entire apartment ...
From $132 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Cozy Chinatown Apartment w free parking spot!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1 ...
From $295 per night (USD)
VRBO
Click For Pricing
Expedia
Large Modern 2BD/2BA Condo in River North- Free Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our chic 2 bedroom, 2 bath condo (Parking Included) in the heart of River North, one of the most sought-after ...
Click For Pricing
Expedia
From $116 per night (USD)
VRBO
Chic 2-bedroom apartment in fabulous Chicago with AC, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your Chicago adventure begins at this 2-bedroom apartment. The space features two bedrooms and a third bedroom used as a ...
From $116 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Chic Modern NEW Loft near United Center, UIC/IMD & Downtown W/ Street Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Discover luxury in our newly renovated 2nd floor loft in Tri-Taylor. With 13-ft ceilings, large windows, brick and moder ...
From $307 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $747 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Cozy 2-Bedroom Apartment with WiFi, AC & More in Hip Logan Square
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming apartment is designed for comfort and convenience, giving you the perfect place to relax after a day of ex ...
From $178 per night (USD)
Expedia
From $1308 per night (USD)
VRBO
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Bedrooms:
5
Bathrooms:
10
Sleeps:
26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1308 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Charming 2-bedroom 1 bathroom Bridgeport Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Chicago unit 2 inviting bedrooms with 1 full bed and 1 bunk bed in Bridgeport . The cozy space includes heating, an ...
From $194 per night (USD)
VRBO
From $280 per night (USD)
VRBO
Chic 2-bedroom apartment with AC, WiFi in vibrant Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a soothing stay at this 2-bedroom apartment in Chicago. The cozy space features 2 queen beds, WiFi, AC, and heatin ...
From $280 per night (USD)
VRBO
From $193 per night (USD)
Expedia
3-bedroom apt .on North Side! Great location between downtown and the airport.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Discover this 3-bedroom gem in Chicago. Remodeled basement unit apartment in the Belmont Cragin neighborhood. Central No ...
From $193 per night (USD)
Expedia
From $119 per night (USD)
VRBO
Chicago Apt 3 Mi to Lake Michigan!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
10 Mi to Downtown Chicago | Private Deck | 1,875 Sq Ft Get to know the Windy City up close and personal while staying a ...
From $119 per night (USD)
VRBO
From $257 per night (USD)
VRBO
Suite Dreams • Designer Style • Central • Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Stylish Home Base in Pilsen: Modern 3BR/2BA condo located in the vibrant East Pilsen/University Village ...
From $257 per night (USD)
VRBO
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 $291 per night (USD)
Expedia
Downtown 2bd #5 +Gym near Park, Lake, Museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $291 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Downtown 3bd #7 near Park+Museums
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because ...
From $410 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Charming 3-bedroom house with AC and WiFi in awesome Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make yourself at home in this 3-bedroom Chicago retreat. This charming house offers all the comforts you need for a wond ...
From $271 per night (USD)
Expedia
From $444 per night (USD)
VRBO
West Loop 2BR, Walk to Top Restaurants, Sleeps 5
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Aqua' is your comfortable 2-bedroom apartment in the West Loop neighborhood. It's a peaceful home with eas ...
From $444 per night (USD)
VRBO
From $474 per night (USD)
Expedia
West Loop PH: Unmatched Views & Private Deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Ideal for families and business travelers seeking spacious luxury in Chicago's West Loop. Our last five guest ...
From $474 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Explore Fulton Market + Retreat in Modern Comfort
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Experience the vibrant heart of Fulton Market at 'The Neo', ideal for sophisticated travelers seeking scenic vi ...
From $533 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Stylish 2BR Retreat in Fulton Market for Getaways
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Experience the perfect blend of design and location at 'The Deco', ideal for sophisticated travelers seeking le ...
From $530 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Exclusive 3BR with Views, Ideal for Tourists
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 'The Rose' offers spacious urban living, steps from Millennium Park. With 90% of our reviews at 5 stars since 2 ...
From $729 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Prime Loop Luxury + City & Train Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: 'The Daisy' offers a unique blend of luxury and convenience, perfect for business travelers and tourists. As ...
From $392 per night (USD)
Expedia
From $702 per night (USD)
VRBO
High-End 3BR Retreat + Steps to Millennium Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 'The Tulip' offers a luxurious escape near top attractions, hosted by a professional team with a 5-year Superho ...
From $702 per night (USD)
VRBO
From $245 per night (USD)
Expedia
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Bedrooms:
1
Bathrooms:
4
Sleeps:
12
Spacious 1200 sqft 3BR 1BA located 10-15 min from Downtown! Tub/Shower Games for adults & kids 5 Smart TVs, free fast wi ...
From $245 per night (USD)
Expedia
From $460 per night (USD)
VRBO
Prime Lincoln Park Views + Modern Amenities Await
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Elm' is your luxury retreat for the ultimate urban getaway, with scenic views and a location that puts eve ...
From $460 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Lincoln Park Getaway: Skyline Views & Luxury
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Pine' is the perfect home base for your Chicago adventure. Top dining and city transit are just outside yo ...
From $483 per night (USD)
Expedia
From $944 per night (USD)
VRBO
Premium 2BR Apartments in Lincoln Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: For families and large groups, 'The Ash' makes your Chicago stay easy, offering two spacious apartments with Wh ...
From $944 per night (USD)
VRBO
From $666 per night (USD)
Expedia
Prime 4BR Penthouse w/ Skyline Views for Families
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Your family's perfect Chicago retreat awaits at 'The Soul,' a spacious 4BR penthouse featuring a kids' room, tw ...
From $666 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Skyline Views in 3BR Apartment w/ Top Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience top-tier comfort in 'The Frame,' the perfect spacious home base for your travels. Don't just take ...
From $526 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Sky-High 2BR w/ Gym & City Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Discover ultimate relaxation at 'The Avant,' perfect for tourists seeking a vibrant stay in Fulton Market. Ou ...
From $533 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Modern 2BR in The Loop + Panoramic City Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Looking for a spotless stay in the heart of the action? 'The Violet' delivers, with unmatched city access and a ...
From $570 per night (USD)
VRBO
From $1025 per night (USD)
VRBO
Event Proximity + Unique Group Retreat in Loop
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Discover 'The Lotus,' your group's private sanctuary in the city, with two stylish apartments placing you steps ...
From $1025 per night (USD)
VRBO
From $538 per night (USD)
VRBO
Top-Floor Oasis: 2BR in Heart of Fulton Market
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Welcome to 'The Dada,' where urban sophistication meets art-filled design. Enjoy premier amenities and the top- ...
From $538 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Chic Fulton Market Oasis + Curated Comfort & Style
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Boho' offers skyline views and resort-style amenities for tourists seeking a unique Chicago getaway. Boo ...
From $531 per night (USD)
Expedia
From $1224 per night (USD)
VRBO
Ideal for Groups: Spacious 2BR in The Loop
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: Discover 'The Poppy,' your group's vibrant home base in The Loop, offering two stylish apartments with breathta ...
From $1224 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Stylish 2BR with Skyline Views Near Riverwalk
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Welcome to 'The Pine,' your stylish home base in the heart of the Windy City. You can relax in total comfort kn ...
From $525 per night (USD)
Expedia
From $1428 per night (USD)
VRBO
Downtown Penthouse Huge Patio with Great View
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Immerse yourself in comfort with our 3600 sqft unit, featuring a 1400 sqft balcony and stunning city panoramas. This spa ...
From $1428 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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)
Expedia
From $286 per night (USD)
VRBO
Stylish 3BR + Free Parking 15-20mins from Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cozy Family-Friendly Apartment Near Downtown Chicago Welcome to our modern, spacious 3-bedroom apartment, ideal for fam ...
From $286 per night (USD)
VRBO
From $1337 per night (USD)
Expedia
Wrigley 4BR Home, Sleeps 10, Firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience Wrigley Ville in this spacious 4-bedroom, 2-bath home, perfect for groups. The house combines two units, offe ...
From $1337 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Wrigleyville 2BR w/Parking, Firepit & Workspace for Remote Work
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the charm of Chicago’s North Side in this cozy 2-bedroom, 1-bathroom apartment, just steps from iconic Wrigley ...
From $484 per night (USD)
VRBO
From $126 per night (USD)
Expedia
Brand New 3B-2BA Unit,4 miles from Downtown Chicago with WiFi, AC, Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your Hestia Certified home in the heart of Chicago! Discover the beauty of Chicago from this 3-bedroom 2-bath ...
From $126 per night (USD)
Expedia
From $441 per night (USD)
VRBO
High-End West Loop 2BR + City Views & Walkability
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: Ideal for tourists and business travelers, 'The Terra' boasts a perfect location for city exploration. With 1 ...
From $441 per night (USD)
VRBO
From $431 per night (USD)
Expedia
West Loop Oasis: Skyline Views + Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Summary: 'The Flame' is your perfect Chicago base for an unforgettable adventure, complete with a private balcony and ex ...
From $431 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Prime 2BR Retreat: Urban Vibes + Views Await
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 'The Lotus' offers an unbeatable downtown experience for urban explorers, complete with remarkable city views a ...
From $572 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Cozy 3-bedroom condo near University of Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come experience this newly renovated, reclaimed red brick 1895 colonial multi-family building. Located 5 mins from the U ...
From $292 per night (USD)
Expedia
From $310 per night (USD)
VRBO
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come stay at our luxurious downtown view in a new construction in Chicago. This centrally located, gated, 3Bedroom, 3Bed ...
From $310 per night (USD)
VRBO
From $114 per night (USD)
Expedia
Amazing River North 1BR w/ Entertainment Area, Pool & Gym, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $114 per night (USD)
Expedia
From $1001 per night (USD)
VRBO
Beautiful, cozy, stylish Bucktown, Wicker Park House, perfect Chicago location.
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Welcome to Rainbow Guest House. This is a designer owned, fully decorated house located in a perfect Bucktown/Wicker Par ...
From $1001 per night (USD)
VRBO
From $435 per night (USD)
Expedia
1 Garage Parking/Skyline Rooftop/PingPong/Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax in this stunning 2-bedroom, 2-bath condo for up to 8 guests, featuring a king bed, one double bed and one ...
From $435 per night (USD)
Expedia
From $406 per night (USD)
VRBO
33rd-Floor Penthouse with Breathtaking Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Experience 'The Harper', a prime 3BR penthouse with panoramic skyline views, perfect for discerning travelers s ...
From $406 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This central location can't be beat! Situated on the border of Lakeview and Wrigleyville and only 1 mile from historic ...
From $187 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Dual Penthouse Retreat: Perfect for Groups
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: The premier choice for corporate retreats and family reunions, 'The Adler' offers two stunning penthouses that ...
From $659 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Breeze of Bronzeville Chicago: 3 bedroom 2 bath 9 mins from downtown chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Chicago with 3 adorable queen bedrooms. This charming house offers WiFi, a washing machine, ...
From $329 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious 3-bedroom apartment in lovely CHICAGO Ukranian VILLAGE w/laundry
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Newly redesigned first floor unit with a sleek, minimalist approach. Equipped with brand new appliances, comfy beds, str ...
Click For Pricing
VRBO
From $397 per night (USD)
Expedia
Spacious & Modern 3BD/2BA Home- Garage Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Chicago’s lively River West & West Loop, you’re just minutes away from some of Chicago’s best d ...
From $397 per night (USD)
Expedia

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