
Apartment vacation rentals in Chicago
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Top-rated apartment rentals in Chicago
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Explore Lincoln Park from a Polished Apartment
This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. Thereâs grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Andersonville 2 bed with modern kitchen + bath
Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

City-Accessible Basement Retreat
Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the cityâs pulse at your doorstep. Your urban retreat awaits!

Rockin' 2Bed steps to shops/food/train
This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. Youâll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Fulton House #1 - Studio Only (Nightly)
Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

*Entire City Apartment 1 block to Train Park Free
Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

Unwind in Style Steps from the Magnificent Mile
Ideally located just half a block from Michigan Avenue, this apartment boasts high ceilings, beautiful wood floors, with thoughtfully appointed rooms for your comfort. You will have everything you need to enjoy your stay in style! PLEASE NOTE: 4th floor walk-up (NO ELEVATOR). There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard leading up to the apartment but never in the apartment.

Belmont Pleasures - hot tub / arcade gaming room
Welcome home! If youâre looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether youâre looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

Modern Apt with style & comfort in Pilsen Chicago
Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Chic retreat near the best of Lakeview & Wrigley
Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!
Popular amenities for Chicago apartment rentals
Weekly apartment rentals

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Renovated LittleVillage Retreat

2-bedroom Apartment in the heart of Oak Park

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Newly-renovated historic home in Logan Square

Spacious 2BR on Quiet St - Free Park/Late Checkout

Beautiful Remodel in Sought After Wrigleyville

Edgewater Studio on Paulina
Private apartment rentals

Sunny Penthouse - Oakwood Beach

Luxury Loft Collection 01 - Terrace - River North

New Build in Pilsen! Spacious 2 Bed 2 Bath Unit

Pilsen Modern Chic Retreat

Hancock Lookout|Steps to Beach&Transit, CHI Views

Garden on Warren

â Bright & Bold 1BR in Roscoe Village + Fireplaceâ

Fantastic West Loop 2 bedroom
Apartment rentals with a hot tub

The Aerial Oasis

Spacious Beautiful Condo

60th Flr Lake Views, A Stay Above It All, Sleeps 5

Skyline Oasis: City & Lake Views

Spacious 1 BR Unit in Wicker Parl|1 FREE G Parking

Modern 4BR Retreat in Vibrant West Town

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Modern 2BR South Loop Apt, McCormick & Wintrust
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,339Â GYD | G$22,386Â GYD | G$24,478Â GYD | G$25,105Â GYD | G$29,289Â GYD | G$30,336Â GYD | G$30,963Â GYD | G$31,591Â GYD | G$27,825Â GYD | G$28,243Â GYD | G$25,733Â GYD | G$23,850Â GYD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about apartment rentals in Chicago

Total vacation rentals
Explore 6,430 vacation rentals in Chicago

Verified guest reviews
Over 322,040 verified reviews to help you choose

Family-friendly vacation rentals
3,160 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 2,310 rentals that welcome pets

Vacation rentals with a pool
860 properties feature pools

Rentals with dedicated workspaces
3,820 properties have a dedicated workspace

Wi-Fi availability
6,330 of Chicago vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chicago rentals

4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
Destinations to explore
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- Rentals with a sauna Chicago
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- Apartment rentals Cook County
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Illinois Beach State Park
- The Beverly Country Club
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Things to do Chicago
- Tours Chicago
- Sports activities Chicago
- Sightseeing Chicago
- Entertainment Chicago
- Food and drink Chicago
- Nature and outdoors Chicago
- Art and culture Chicago
- Things to do Cook County
- Nature and outdoors Cook County
- Sightseeing Cook County
- Tours Cook County
- Art and culture Cook County
- Sports activities Cook County
- Food and drink Cook County
- Entertainment Cook County
- Things to do Illinois
- Tours Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sports activities Illinois
- Nature and outdoors Illinois
- Things to do United States
- Art and culture United States
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