
Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.

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. There’s 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.

Professional's Playground (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Fairfield Flat, Airy Vintage Rehab
This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, and Douglass Park. Pilsen and West Loop night life a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing. Great for couples or friends, though parents have expressed frustration with the hard, or uneven surfaces, and the stairs.

Victorian Guest Suite in Old Town
This private guest suite is the restored 1st floor of my Victorian era single family home. The space has a private ground floor entrance with small patio, located in the “Old Town Historic District”. Decor is Mid Century Modern. Located 1 block north of Sedgwick train station, bus stop across the street, 5 minute walk to the lake, 1/2 hour lakeside walk to downtown. Great restaurants nearby. Only registered guests are allowed on the premises. Please see booking requirements in house rules

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.

Cute, Clean, Cozy Apartment in Pilsen
Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Humboldt Park Loft
Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Sophisticated Flat in Historic Building
Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Sunny Logan Square Artists' home
2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

Walk to Oak Park from this Newly Remodeled Gem
This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

Lavish 2BR/2BA Loft I Next to Grant Park & Museums
Enjoy Chicago in our modern & spacious 2-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Penthouse Near Wrigley Field
This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.
Popular amenities for Chicago apartment rentals
Weekly apartment rentals

Bucktown Brick Cottage Apartment

Renovated LittleVillage Retreat

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Sunny 1 bedroom apartment 1 block from restaurants

Urban Oasis with Skylights and Cozy Queen Beds

Logan Square Studio

The Grotto of Logan Square

Spacious Studio in Prime Location
Private apartment rentals

Stunning 2bd 1bath w/free parking, W/D & fireplace

Archways at the Lincoln Park Zoo 2bed/2ba

Spectacular Pilsen Studio for 2!

Charming Two Bedroom in Wicker Park

Minty Fresh • Vintage Lincoln Park Flat

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Turquoise Wonder - Clean, Cozy & Stylish Apt

Garden on Warren
Apartment rentals with a hot tub

Luxe 67th Flr 2BR: Endless Lake Views, Top Skydeck

Luxury 3BD Penthouse – Private Patio+Skyline Views

Skyline Oasis: City & Lake Views

Level One Bedroom Suite | Fulton Market

Chic 1 BR w 1 G Parking| W Park Nightlife nearby

Belmont Pleasures - hot tub / arcade gaming room

Executive Retreat Gym Sauna Whirlpool Steam Shower

Checkerboard Studio, Private Outdoor Hot Tub, Yard
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £76 | £79 | £87 | £89 | £104 | £107 | £110 | £112 | £99 | £100 | £89 | £85 |
| 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 flat rentals in Chicago

Total holiday rentals
Explore 6,570 holiday rentals in Chicago

Verified guest reviews
Over 333,260 verified reviews to help you choose

Family-friendly holiday rentals
3,250 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 2,400 rentals that welcome pets

Holiday rentals with a pool
890 properties feature pools

Rentals with dedicated workspaces
3,990 properties have a dedicated workspace

Wifi availability
6,460 of Chicago holiday rentals include wifi 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
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- University of Chicago
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