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Chicago Rentals

From $317 per night (USD)
VRBO
Feelin’ Nauti Near Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I took a perfectly nice little flat on a beautiful street and filled it with great things...I want my guests t ...
From $317 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Fifty Shades of Greige
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: I’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a sus ...
From $288 per night (USD)
Expedia
From $265 per night (USD)
VRBO
The Sassy Sanctuary at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $265 per night (USD)
VRBO
From $230 per night (USD)
Expedia
The Shingle Life near Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I took a perfectly nice little flat on a beautiful street and filled it with great things...I want my guests t ...
From $230 per night (USD)
Expedia
From $234 per night (USD)
VRBO
The Lilac Loveshack at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $234 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Campy! Wrigley Campground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $245 per night (USD)
Expedia
From $217 per night (USD)
VRBO
A Hand-some Place Near Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I’m an interior designer and longtime Superhost who believes you deserve better than scratchy sheets and a sus ...
From $217 per night (USD)
VRBO
From $341 per night (USD)
Expedia
The Fratterhorn at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $341 per night (USD)
Expedia
From $230 per night (USD)
VRBO
No Place Like Gnome at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $230 per night (USD)
VRBO
From $229 per night (USD)
Expedia
A Novel Situation at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $229 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Keepin’ it Golden at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $250 per night (USD)
VRBO
From $308 per night (USD)
Expedia
The Codfather at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The location literally can't be beat, with the apartment a short walk from Wrigley Field, the bustling Southpo ...
From $308 per night (USD)
Expedia
From $393 per night (USD)
VRBO
The Ivy Flat | Designer 4BR Steps to Wrigley Field
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: This 4BR/2BA apartment is a 7-minute walk from Wrigley Field and perfect for groups. There's tons of room to s ...
From $393 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Sunnyside Up! • Vintage 1 Bed at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: My new place has lots of room to spread out and all of the quirky charm that vintage buildings offer up. The l ...
From $254 per night (USD)
Expedia
From $403 per night (USD)
VRBO
The Mason - Luxe 2BR Designer Flat in Bucktown/WP
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: We invite you to spend your next trip in this beautifully remodeled 2BR flat in Chicago's iconic Wicker Park n ...
From $403 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Feelin’ Blue-tiful at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This is such a lovely spot and I think you will quite like it. The space features wonderful large windows in a ...
From $240 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Taj Ma-small at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I think you are just going to love my apartment. The space features wonderful large windows in both rooms and ...
From $229 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Tickled Pink • Vintage 1 Bed at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: My new place has lots of room to spread out and all of the quirky charm that vintage buildings offer up. The l ...
From $254 per night (USD)
Expedia
From $787 per night (USD)
VRBO
Pristine Gold Coast 3BD - 2BA - Free Parking - Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FREE GARAGE PARKING! Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and indoor games. Experience the ...
From $787 per night (USD)
VRBO
From $1493 per night (USD)
Expedia
Gold Coast Pristine 5BR - 3.5BA - Patio - Parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Free Garage Parking!! Experience the best of Chicago in this stunning multi-level Gold Coast residence. Perfect for gro ...
From $1493 per night (USD)
Expedia
From $1444 per night (USD)
VRBO
Gold Coast Home - Rooftop - PoolTable - Parking - Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this st ...
From $1444 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Pristine Chicago Home - 3BD - 2BA - Free Parking - 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Free Parking!! Step into luxury in this modern loft with 3 bedrooms, and 2 bathrooms & experience the feeling of being a ...
From $342 per night (USD)
Expedia
From $627 per night (USD)
VRBO
Pool Table! Pet-Friendly Haven 6 Mi to Rate Field
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1 Mi to Red Line | Main Living Area + Social Lounge | Spacious Backyard | 10 Mi to Downtown Designed for groups who lov ...
From $627 per night (USD)
VRBO
From $725 per night (USD)
Expedia
2,400 SF 4BR + 2 Parking | Steps to Wrigley
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience The Clubhouse at Wrigley Thoughtfully designed for gathering, relaxing, and making memories, The Clubhouse a ...
From $725 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Pristine 2BD - 2.5BD Duplex - Chicago - Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover comfort and privacy in our stylish duplex apartment just steps from Lake Michigan. This 2-bedroom, 2.5-bath hom ...
From $342 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Elegant Historic Duplex in Old Town • Lincoln Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the charm of Chicago’s historic Old Town from this beautiful duplex on a quiet, tree-lined street. Steps to W ...
From $613 per night (USD)
Expedia
From $106 per night (USD)
VRBO
Cozy 1 bed, furnished apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the beauty of Wrigelyville in this furnished 1-bedroom apartment. Step into a peaceful space where comfort meet ...
From $106 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Luxury Wrigley Getaway | 2BR + Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the best of Wrigleyville in this stylish 2-bedroom retreat with free parking. Perfect for couples, small fami ...
From $479 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Vibrant Getaway in the Windy City of Chicago
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this 3-bedroom one bath apartment in Chicago offers the perfect blend of city proximity and res ...
From $157 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Chicago O’Hare Modern Hotel‑Style Stay w/parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your stylish hotel‑inspired getaway near Chicago’s O’Hare Airport! This bright and spacious 1‑bedroom condo i ...
From $334 per night (USD)
Expedia
From $620 per night (USD)
VRBO
Wrigley Luxe Stay | 3BR | Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the comfort of our beautifully designed 3-bedroom home just minutes from Wrigley Field! Perfect for families, frie ...
From $620 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Luxury 4BR Home with Spa Tub & fire place Near UChicago & Obama Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, g ...
From $426 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Chicago Home with gym - 15 min to O’Hare & Rosemont
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to my home! This is my primary residence, thoughtfully prepared for guests while I'm away. The home features thr ...
From $301 per night (USD)
VRBO
From $401 per night (USD)
VRBO
NEW! Ukrainian Village 2 BD/2BA - Steps from Division!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unwind in my bright, airy 2BR/2BA garden condo on a quiet tree-lined block in popular Ukrainian Village. The home featu ...
From $401 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Stunning 3bdrm, steps to North Eastern University, Luxurious, Gourmet kitchen🌟
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Greetings from “The Bernard at Hollywood Park” located on the Northside of Chicago! Our luxury three bedroom, one bath a ...
From $574 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Beautiful Mid-Century Oasis in South Shore.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This mid century masterpiece is one of kind, offering a beautiful open living space with lots of natural light through a ...
From $531 per night (USD)
Expedia
From $686 per night (USD)
VRBO
3 Units | Near Chicago River | Downtown Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Chicago's River North neighborhood, this hotel offers convenient access to the vibrant dining and nightlife s ...
From $686 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Space: Welcome to our beautiful Logan Square apartment! Experience Chicago like a local in this spacious 2-bedroom, ...
From $328 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Luxury Penthouse Collection PH2 - Fulton Market
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $337 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Luxury Penthouse Collection PH1 - Fulton Market
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $384 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Luxury Penthouse Collection PH4 - Fulton Market
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $485 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Luxury Penthouse Collection PH3 - Fulton Market
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Summary: BRAND NEW PENTHOUSE IN FULTON MARKET! Enjoy your new private penthouse in one of Chicago's newest and mos ...
From $333 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Near UChicago, 3BR Apt, Parking, W/D, 2 Workspaces
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Work-ready 3BR, 2BA apartment located just minutes from UChicago and several major hospitals. Once inside, everything is ...
From $255 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Brown Line Lounge | Curated Moody
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Welcome to Brown Line Lounge. Samantha and I designed this 3BR/2BA North Center apartment around every ...
From $243 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Modern 3BR Apt Near United Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this brand-new, stylish 3-bed, 2-bath Chicago apartment! Featuring a chic contemporary design with plush velve ...
From $364 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Spacious 7-bedroom house in gorgeous Lincoln Park Chicago with AC
Bedrooms:
4
Bathrooms:
7
Sleeps:
18
Your Chicago adventure begins at this 7-bedroom house. This charming home features a mix of cozy beds, including 4 queen ...
From $835 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Near Parks & Eats! Elegant Southwest Chicago Home
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Quiet Suburban Neighborhood | Ideal for Traveling Medical Professionals Feel at home from day one at this beautifully a ...
From $172 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Spacious 3-bedroom apartment in brilliant Chicago with AC Logan Square area,
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This memorable apartment is the perfect home base for your trip to Chicago. Guests will find three full beds spread acro ...
From $620 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Logan Square Boho Getaway - Sleeps 6 - Remodeled
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this cheerful, pet friendly 700 sqft Chicago retreat for 4-6 guests! Newly renovated garden apartment and in a ...
From $314 per night (USD)
VRBO
From $3640 per night (USD)
Expedia
Sleek New 6BR Greystone - Rooftop, In-Law Ste, Walk to Wrigley & Block to Train
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Welcome to your ultimate Chicago getaway. This brand-new, ultra-spacious Greystone sits perfectly at the intersection of ...
From $3640 per night (USD)
Expedia
From $144 per night (USD)
VRBO
Stylish 2BR Near UChicago – Easy Downtown Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern and stylish 2-bedroom apartment near the University of Chicago. Fully furnished with a stocked kitchen, blackout ...
From $144 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Cozy 1 Bedroom Apartment 20 Minutes from Downtown Chicago
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your private Chicago retreat! Conveniently located just 20 minutes from Downtown Chicago and 5 minutes from t ...
From $455 per night (USD)
Expedia
From $205 per night (USD)
VRBO
2-bedroom apartment in awesome Chicago with cool AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Cozy Study — Apartment 1: a private, fully furnished 2 bedroom, 2 bathroom unit in Bronzeville, perfect f ...
From $205 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Wrigleyville Oasis • Modern Comfort Steps from Wrigley Field
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your Wrigleyville Oasis—an inviting, thoughtfully designed apartment perfect for travelers seeking comfort, c ...
From $408 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away on a quiet, tree-lined street in Chicago’s Uptown / Sheridan Park, this beautifully renovated 2-bedroom, 1-b ...
From $260 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Cozy 2BR Near McCormick & Wintrust with Optional Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
When you step inside this bright South Loop suite, the energy of the city fades away. Sunlight fills the space, creating ...
From $185 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Chicago Gem Near Downtown Steps from La Catedral Café : Family and Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Casa De Alma Enjoy a comfortable Chicago stay in a convenient neighborhood location with easy access to downt ...
From $311 per night (USD)
VRBO
From $113 per night (USD)
Expedia
Blueground | Edgewater, gym, nr Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this sophisticated two bedroom Blueground apartment. You’ll love c ...
From $113 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Lux New Hyde Park Apt by U Chicago, Museum of Science & Industry w/Peloton
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Luxury Hyde Park Retreat — Just Steps from History, Culture & UChicago Luxury 3BR/2BA apartment in a fu ...
From $406 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Relax & Unwind Private, Comfortable, & Convenient
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom apartment is perfect for your escape to Chicago. Featuring three queen beds, it offers a marvelous space ...
From $434 per night (USD)
Expedia
From $893 per night (USD)
VRBO
The Boho House • Two Private Suites + Parking
Bedrooms:
4
Bathrooms:
1
Sleeps:
12
Two private suites. One unforgettable stay. Perfect for groups who want to be together—without sacrificing space. Enjoy ...
From $893 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Designer 3BR Near Beach & Obama Center
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $817 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Private Yard Near Beach & Obama Center
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $808 per night (USD)
VRBO
From $914 per night (USD)
Expedia
The Zen Duplex: Two Private Suites for Groups
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the "Adjoining Suite" life. This dual-level Zen retreat offers the perfect balance for families or groups: st ...
From $914 per night (USD)
Expedia
From $1026 per night (USD)
VRBO
Designer Home | Steps to the Obama Center & Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine ...
From $1026 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Chic & Comfy 3-bedroom apartment in Logan Square, family friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to our home, situated in a charming residential area of Logan Square, a vibrant neighborhood. Enjoy being walkin ...
From $295 per night (USD)
VRBO
From $860 per night (USD)
VRBO
Luxury Gold Coast Duplex -8 Bedrooms 3 Bath
Bedrooms:
3
Bathrooms:
8
Sleeps:
15
Summary: Whether you're planning a family reunion, group getaway, corporate retreat, or celebrating a special occasion, ...
From $860 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Studio Plus at Hilton Grand Vacations Club Chicago Magnificent Mile Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located between Chicago's Magnificent Mile and Navy Pier, Chicago Magnificent Mile, a Hilton Grand Vacations Club, offer ...
From $177 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Chicago 1-bed condo Close to Everything Balcony Washer Dryer Gym Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This property is spacious and luxurious with its own private balcony and in unit washer and dryer, walk in closet, wood ...
From $154 per night (USD)
VRBO
From $135 per night (USD)
VRBO
Sunny Pilsen 2 Bed 1 Bath Apt W/Private Office and Garage Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
AVAILABLE MAY 1ST, 2026 - Fully furnished, second floor 2 bed 1 bath apartment with an office for rent in sunny Pilsen. ...
From $135 per night (USD)
VRBO
From $839 per night (USD)
VRBO
Retreat House with Outdoor Hot Tub & Barrel Sauna
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this pleasant house in Chicago. With three bedrooms featuring a king bed, two queen beds, and a pack n play, ...
From $839 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Pilsen Retreat: 4BR 3BA near Downtown Chicago
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Discover one of Chicago's most vibrant neighborhoods from this stylish 4-bedroom retreat in vibrant Pilsen. St ...
From $306 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Lovely 3-bedroom condo Walking Distance to United Center and Futon for extra bed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chicago is waiting for you at this 3-bedroom condo. Inside, guests find two full beds and one queen bed, also included a ...
From $393 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Spacious 3BR near United Center: Deck & Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Experience ultimate comfort in this charming home, steps away from the United Center. Catch a game or concert, ...
From $308 per night (USD)
VRBO
From $115 per night (USD)
VRBO
Detached, private, spacious, free garage, fast wifi, 5min to metra in Ravenswood
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fully renovated in July 2025, this charming detached coach house from 1897 blends historic character with modern comfort ...
From $115 per night (USD)
VRBO
From $158 per night (USD)
VRBO
West Loop Living • New Furniture • Garage Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your home away from home in the heart of Chicago's West Loop. This thoughtfully furnished high-rise condo com ...
From $158 per night (USD)
VRBO
From $154 per night (USD)
VRBO
2-bedroom 1 bath stylish apartment in nice Chicago for relaxing stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable apartment is the perfect home base for your trip to Chicago. Guests will enjoy two comfortable bedrooms, ...
From $154 per night (USD)
VRBO
From $222 per night (USD)
VRBO
The Gilded Grid | Sleeps 8
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience modern luxury just moments from Wrigley Field in this brand-new 4-bedroom, 3.5-bath duplex that sleeps up to ...
From $222 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Quirky Quarters at Wrigley
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: I think you are just going to love my apartment. The space features wonderful large street level windows in th ...
From $250 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Luxury Penthouse COMBO 07/04 Terrace | River North
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Enjoy the combination of your luxury two-story designer styled apartment located in River North - the city's c ...
From $606 per night (USD)
VRBO
From $661 per night (USD)
VRBO
Luxury Penthouse COMBO 07/02 Terrace | River North
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Summary: Enjoy the combination of your luxury designer styled apartment located in River North - the city's center of n ...
From $661 per night (USD)
VRBO
From $330 per night (USD)
VRBO
Modern Design 3 BDR Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover your stylish retreat in Avondale! This beautifully appointed 3-bedroom apartment seamlessly blends modern luxur ...
From $330 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Shorter Walk To Wrigley Than A Home Run
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This unit is a shorter walk to Wrigley Stadium than a home run. Catty-corner to Wrigley Field, you'll be at the center ...
From $524 per night (USD)
VRBO
From $129 per night (USD)
VRBO
Peaceful 3-bedroom apartment with AC in vibrant Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this marvelous apartment in Chicago. With three comfortable bedrooms and two bathrooms, guests have plenty of ...
From $129 per night (USD)
VRBO
From $108 per night (USD)
VRBO
Cozy Stay in Chicago/ 2 Bedroom/ Up to 4 People/32+ Days Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for a cozy, convenient place to stay in Chicago? This charming apartment in Roger’s Park is the perfect. This fu ...
From $108 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Chicago is waiting for you! Enjoy our newly remodeled impeccably clean, cozy and peaceful 1-bedroom supreme comfort in t ...
From $205 per night (USD)
VRBO
From $170 per night (USD)
VRBO
2-bedroom house on a quiet, tree-lined street with modern amenities throughout
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
A Comfortable Chicago Home Base — Pet-Friendly & Work-Ready Welcome to your Chicago home away from home, set in a quiet ...
From $170 per night (USD)
VRBO
From $289 per night (USD)
VRBO
West Town Gem: 3-Bedroom Spacious Apartment
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to your home away from home in Chicago's charming West Town neighborhood. Start your morning with the ...
From $289 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Stylish 1BR/1BA Near Lake in Rogers Park + Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Rogers Park is Chicago’s northernmost lakefront neighborhood, known for its beaches, parks, and tree-lined streets lined ...
From $202 per night (USD)
VRBO
From $233 per night (USD)
VRBO
West Town Lookout • Spacious • Modern • Sleeps 4
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a bright, open-concept home where oversized windows flood the space with natural light and high ceilings creat ...
From $233 per night (USD)
VRBO
From $897 per night (USD)
VRBO
Luxury Oasis in the Heart of the City with Incredible Private Roof Deck & Patio
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stunning designer 3 bedroom-3 bathroom home in Chicago's trendy Ukrainian Village—minutes from the Loop & steps to the t ...
From $897 per night (USD)
VRBO
From $246 per night (USD)
VRBO
Welcome to our 2-Bed Apartment in West Town for 7!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Summary: Experience Chicago from the heart of vibrant West Town. Start your morning with coffee in a bright, open livin ...
From $246 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Cozy 1BR Near Loyola University • Fast WiFi • Walk to Dining & Transit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Settle into this cozy and inviting apartment—perfect for travelers in town for school, work, or a relaxing escape. Ideal ...
From $197 per night (USD)
VRBO
From $205 per night (USD)
VRBO
2BR/1BA Apt w/ Modern Amenities Rogers Park + Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rogers Park is Chicago’s northernmost lakefront neighborhood, known for its beaches, parks, and tree-lined streets lined ...
From $205 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Comfy Condo - Gym, Free Parking & Modern Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience the best of Chicago's lakefront from this Edgewater retreat, just minutes from the Granville Red Li ...
From $260 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Modern Furnished 2BR in Pilsen Near Medical District & Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a relaxed, stylish stay in this fully furnished 2-bedroom, 1-bath apartment located in Chicago’s vibrant Pilsen ne ...
From $299 per night (USD)
VRBO
From $213 per night (USD)
VRBO
Spacious Modern Pilsen Retreat | Sleeps 8 | Near Downtown Chicago
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to your home away from home in the heart of Chicago's vibrant Pilsen neighborhood! Entire apartment id ...
From $213 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Edgewater Apt with Free Parking, Gym, City Living
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience the charm of Chicago's Edgewater neighborhood, where lakefront mornings and local cafés are just mo ...
From $207 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Chic 2BR Apartment in Edgewater: Gym & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience the best of Chicago's lakefront from this Edgewater retreat, just minutes from the Granville Red Li ...
From $221 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Andi's Treehouse
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
We open our home to guests during the summer. You will have the whole top floor of this historic 1889 4 story greystone ...
From $403 per night (USD)
VRBO

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