Chicago Rentals
From $382 per night (USD)VRBO
#1103 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $382 per night (USD)VRBO
From $372 per night (USD)VRBO
#1812 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $372 per night (USD)VRBO
From $415 per night (USD)VRBO
#1402 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $415 per night (USD)VRBO
From $380 per night (USD)VRBO
#1916 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $380 per night (USD)VRBO
From $675 per night (USD)VRBO
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Live like a local in one of Chicago’s best neighborhoods! Located in a family-owned boutique building in the vibrant and ...
From $675 per night (USD)VRBO
From $344 per night (USD)Expedia
BEAUTIFUL 4/20 FRIENDLY 2 BR 2 BA DUPLEX -TWO FLOORS - IN SIZZLING SOUTH SHORE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We invite you to our beautiful home, minutes from Downtown, Hyde Park, Golfing, Fishing, and the Beach! Floor 1 feature ...
From $344 per night (USD)Expedia
From $617 per night (USD)VRBO
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen an ...
From $617 per night (USD)VRBO
From $141 per night (USD)Expedia
Spacious 3 bdrm 1.5 bath; Renovated Woodlawn; Incredible Access; UChicago; OPC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This large commodious home is the ultimate place to relax, visit and/or collaborate in our beautiful city. Near the site ...
From $141 per night (USD)Expedia
From $315 per night (USD)VRBO
Trendy West Town Flat - 2 bed / 1.5 bath with parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Find your wanderlust in this perfectly located West Town condo. Situated between Chicago’s West Loop and Wicker Park ne ...
From $315 per night (USD)VRBO
From $569 per night (USD)Expedia
The Greenleaf House—Whole House
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 12
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gat ...
From $569 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 $371 per night (USD)VRBO
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*Please inquire before requesting to book* 4 bedroom 2 bath apartment. In the Historic up and coming kenwood neighbor ...
From $371 per night (USD)VRBO
From $870 per night (USD)VRBO
Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural D
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 24
Summary: 2 beautiful side-by-side apartments comprising 5,000 square feet (the entire 2nd floor) of a brick-and-timber l ...
From $870 per night (USD)VRBO
From $397 per night (USD)VRBO
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Summary: Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of ...
From $397 per night (USD)VRBO
From $376 per night (USD)VRBO
Luxury, spacious first floor brownstone in east Lincoln Park
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the best of Chicago’s neighborhoods, parks and lakefront from the comfort of this 2400 square foot home with two s ...
From $376 per night (USD)VRBO
From $293 per night (USD)VRBO
#1516 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $293 per night (USD)VRBO
From $401 per night (USD)VRBO
#1902 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $401 per night (USD)VRBO
From $382 per night (USD)VRBO
#2003 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $382 per night (USD)VRBO
From $408 per night (USD)VRBO
#1401 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $408 per night (USD)VRBO
From $311 per night (USD)VRBO
#1515 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $311 per night (USD)VRBO
From $326 per night (USD)VRBO
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in MODERN Chicago? Our NEWLY FINISHED 2-level masterpiece has IMPECCABLE DESIGN, 4 bedrooms, IN-U ...
From $326 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 $1941 per night (USD)VRBO
Luxurious Four-Level Home with Personal Touches Everywhere
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 17
Cook in a dream kitchen with top-of-the-line appliances at this sprawling and luxurious home located on a quiet, one-way ...
From $1941 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 $273 per night (USD)Expedia
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
1700 sqft penthouse in the historic west end of the West Loop. Nestled on a quiet street, minutes away from incredible r ...
From $273 per night (USD)Expedia
From $432 per night (USD)VRBO
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $432 per night (USD)VRBO
From $531 per night (USD)VRBO
Lincoln Park Charm Near Everything + On site Parking Spot Included
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay at this gorgeous, clean, renovated, top-floor apartment in beautiful Lincoln Park. The unit is located on a qu ...
From $531 per night (USD)VRBO
From $455 per night (USD)VRBO
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, two separate living ...
From $455 per night (USD)VRBO
From $313 per night (USD)Expedia
Walking distance to restaurants, shops and Lake Michigan,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Residence on the Avenue. A Spacious 1700 sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined ...
From $313 per night (USD)Expedia
From $116 per night (USD)VRBO
Sleek 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 spacious one bedroom Blueground apartment. You’ll love coming ...
From $116 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 $88 per night (USD)VRBO
Elegant Lakeview 1BR w/ Gym, Pool, 1 block to Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Lake View East furnished one be ...
From $88 per night (USD)VRBO
From $425 per night (USD)VRBO
#1501 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $425 per night (USD)VRBO
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 $263 per night (USD)Expedia
Great Location-Beautiful Friendly Andersonville Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
City of Chicago Vacation LICENSE NO.: 2209341 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful t ...
From $263 per night (USD)Expedia
From $255 per night (USD)VRBO
Walking distance to restaurants, shops and Lake Michigan,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Residence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. We are a ...
From $255 per night (USD)VRBO
From $595 per night (USD)Expedia
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are happy to announce our 2nd Wrigleyville location. The Wrigleyville VIP sits just behind the Hotel Zachary, on the ...
From $595 per night (USD)Expedia
From $302 per night (USD)VRBO
One block from Lincoln Park and the zoo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our place is a newly renovated.! You'll love the kitchen, the fireplace, the outdoor deck and it's coziness. Perfect for ...
From $302 per night (USD)VRBO
From $385 per night (USD)VRBO
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local in one of Chicago’s best neighborhoods at a top rated property! Located in a family-owned boutique bui ...
From $385 per night (USD)VRBO
From $159 per night (USD)VRBO
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
What guests like most? Super clean. Super comfortable. Super Host. Full use of second story fully furnished private apa ...
From $159 per night (USD)VRBO
From $181 per night (USD)Expedia
iKlektik House Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully furnished one bedroom in Ukrainian Village/West Town. Voted best top ten neighborhood in the United States. Close ...
From $181 per night (USD)Expedia
From $156 per night (USD)VRBO
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)VRBO
From $171 per night (USD)Expedia
Angie & Mike's Nest!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated three bedroom & 1 bath apartment with stainless steel appliances. The space The apartment is in the se ...
From $171 per night (USD)Expedia
From $284 per night (USD)VRBO
✨|Beautiful|Comfy|1br|✨LincolnSq.|Near Wrigley| ✨
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $284 per night (USD)VRBO
From $350 per night (USD)Expedia
✨Rustic Studio Apartment Heart of Lincoln Square✨
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $350 per night (USD)Expedia
From $347 per night (USD)VRBO
Inviting Stylish Home with Covered Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan mai ...
From $347 per night (USD)VRBO
From $318 per night (USD)Expedia
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $318 per night (USD)Expedia
From $325 per night (USD)VRBO
🌟Homey|Snuggly|Modern|1BR Lakeview - Near Wrigley🌟
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lakeview is home to Wrigleyville, Wrigley field home of the Chicago Cubs and Belmont theatre district which has over 30 ...
From $325 per night (USD)VRBO
From $201 per night (USD)Expedia
New 3BR Residence Adjacent to Wrigley Field - Outdoor Patio - BBQ Grill
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Everything about this residence is top of the line, first class and immaculately clean. This is a designer decorated thr ...
From $201 per night (USD)Expedia
From $422 per night (USD)VRBO
Soft Palate & Warm Bricks At A Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $422 per night (USD)VRBO
From $777 per night (USD)Expedia
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)Expedia
From $561 per night (USD)VRBO
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lincoln Park is one of the most coveted areas to live or stay in Chicago. DePaul University is less than a block away. L ...
From $561 per night (USD)VRBO
From $228 per night (USD)Expedia
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located right off main bustling streets in Logan Square, i.e. the famous Milwaukee Ave, you definitely won’t need a car ...
From $228 per night (USD)Expedia
From $238 per night (USD)VRBO
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a beautifully remodeled, modern, spacious, and luxuriously furnished 3 bedroom, 2 bath private city apartment. ...
From $238 per night (USD)VRBO
From $135 per night (USD)Expedia
Modern Lincoln Park Hideaway 1 Bed and 1Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently fully renovated sanctuary in west Lincoln Park. Enjoy the abundant restaurants, shopping, lake and beaches near ...
From $135 per night (USD)Expedia
From $252 per night (USD)VRBO
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in the heart of Chicago's premier entertainment district • Walk Score 93 (“Walker’s Paradise”) • Free street par ...
From $252 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 $273 per night (USD)Expedia
Bright Streeterville 2BR w/ Gym, Pool, near Navy Pier, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Streeterville furnished two bedroom apar ...
From $273 per night (USD)Expedia
From $571 per night (USD)VRBO
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 24
Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home brought to you by ...
From $571 per night (USD)VRBO
From $302 per night (USD)Expedia
52nd Floor MagMile Penthouse Views Fireplace Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Penthouses at Grand Plaza PH#9 Experience elevated city living from this stunning penthouse, soaring 52 sto ...
From $302 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 $404 per night (USD)VRBO
Historic 1920s Private Bungalow Near Logan Square!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. The only room ...
From $404 per night (USD)VRBO
From $225 per night (USD)Expedia
Luxurious 3Br with parking on premises 🌔
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This unique place has a style all its own. Modern/cozy feel. Freshly renovated. Enjoy the hassle-free parking on the pre ...
From $225 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
Click For PricingExpedia
Large 12 room house steps to Park, Shopping and Restaurants, 10 minutes to beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Large Jumbo Georgian two story brick house centrally located on the North side of Chicago in a quiet neighborhood with t ...
Click For PricingExpedia
From $219 per night (USD)VRBO
Belmont House, Classy & Chic/walk to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous home is smack-dab in one of the hottest neighborhoods in Chicago, a 3/4 mile 15 minute walk to Wrigley Fie ...
From $219 per night (USD)VRBO
From $340 per night (USD)VRBO
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Why pay $$$ Chi parking when you have a 2 CAR GARAGE DOWNTOWN? Our 4br/3.5ba rowhome has 4 levels & 2 ROOFTOPS; ...
From $340 per night (USD)VRBO
From $164 per night (USD)VRBO
Bright/Cozy/Hip 2/1 Apt | Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Enjoy Chicago as a Chicagoan and welcome to the historic now hip neighborhood of Logan Square. It is a must see ...
From $164 per night (USD)VRBO
From $376 per night (USD)Expedia
Private Historic Coach House Wicker Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Location, location, location! Private quiet clean coach house with two bedrooms and one bath in the heart of Wicker Park ...
From $376 per night (USD)Expedia
Click For PricingVRBO
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great 3Br 2Ba condo with a king bed in the primary bedroom. You'll feel at home with all the amenities just 5 miles from ...
Click For PricingVRBO
From $447 per night (USD)Expedia
The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Designer urban feel - completely rehabbed - reclaimed wood beams - full walk in glass master shower with an exposed bric ...
From $447 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 $353 per night (USD)VRBO
Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $353 per night (USD)VRBO
From $369 per night (USD)Expedia
Vintage Wrigleyville Apartment + Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious apartment in the heart of Wrigleyville, two blocks to public transportation. Located in an 1911 graystone, priv ...
From $369 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 $115 per night (USD)Expedia
Sunny West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, 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 $115 per night (USD)Expedia
From $89 per night (USD)VRBO
Ideal West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, 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 $89 per night (USD)VRBO
From $96 per night (USD)Expedia
Cozy Loop 1BR w/ Deck, Gym, W/D, nr. West Loop & the L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $96 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 $131 per night (USD)Expedia
Luxe West Loop 1BR w/ Pool, Coworking & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $131 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 $297 per night (USD)Expedia
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)Expedia
From $344 per night (USD)VRBO
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $344 per night (USD)VRBO
From $291 per night (USD)Expedia
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
𝐖𝐞𝐥𝐜𝐨𝐦𝐞 𝐭𝐨 𝐨𝐮𝐫 𝐌𝐈𝐜𝐡𝐢𝐠𝐚𝐧 𝐀𝐯𝐞𝐧𝐮𝐞, 𝐆𝐫𝐚𝐧𝐭 𝐏𝐚𝐫𝐤, 𝐌𝐮𝐬𝐞𝐮𝐦 𝐂𝐚𝐦𝐩𝐮𝐬 2𝐛𝐞𝐝/2𝐛𝐚𝐭 ...
From $291 per night (USD)Expedia
From $313 per night (USD)VRBO
Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $313 per night (USD)VRBO
From $808 per night (USD)VRBO
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $808 per night (USD)VRBO
From $337 per night (USD)VRBO
Kasa | Traditional 1 BD + Fast Wifi | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $337 per night (USD)VRBO
From $358 per night (USD)VRBO
Kasa | Inviting 1 BD + Pet Friendly | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $358 per night (USD)VRBO
From $374 per night (USD)VRBO
Kasa | Classic 1 BD + Gym Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $374 per night (USD)VRBO
From $438 per night (USD)VRBO
Kasa | Modern 1 BD + Gym Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $438 per night (USD)VRBO