
Apartment holiday rentals in Chicago
Find and book unique apartments on Airbnb
Quick stats about apartment rentals in Chicago

Total holiday rentals
Explore 1,080 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 71,960 verified reviews to help you choose

Family-friendly holiday rentals
650 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
630 properties have a dedicated workspace

Wifi availability
1,060 of Chicago holiday rentals include wifi access

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

4.8 Average rating
Chicago stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.

Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Dim the lights, play chilled tunes through the Bluetooth speakers, and snuggle up on the caramel suede sofa at this welcoming home. Wander the polished hardwood floors, pluck spices from the open shelving, and serve dinner on the kitchen island. Cleaning fee is $350 for stays of 30 days or less; additional Flat $150 per 30-days for longer term stays. Also, check out our other two listings in the building. Soft Leather & Warm Bricks in Stylish New Home: airbnb.com//h/softleather-warmbricks Soft Palate & Warm Bricks at a Rogers Park Home: airbnb.com//h/softpalate-warmbricks Meet NEW and CHARM with exposed brick,dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open shelving, gourmet kitchen seats 6, stainless steel appliances, wood counters,5 range oven w/Broan hood, soft close cabinets,coffee machine or walk to Starbucks or french coral coffee around the corner. Grocery store(Jewel),Dry Cleaners(will provide you with a discount for staying at The Clark),UPS,Walgreens, Marshalls,LA Fitness, wine shop,Red Line, Metra, CTA Transportation,Evanston,Lake,Beaches, and Restaurants all in walking distance.Loyola and Northwestern 10 minutes away...Only bring your clothes and your ready to go! Free Wifi,Keyless Entry,Towels,Bedding,Ready to cook kitchen, 1 Free Parking space and $25 per diem for each additional vehicle. The entire unit is for your guests alone. Not a shared space. Reservations are set for(4) four people. Additional charges of $40 per person per diem applies. Space accommodates up to 6 guests. Chicago is an Amazing City and I'm here to answer and help out any way I can. Meeting guests upon their arrival is what helps guests become acclimated with the space and provides a sense of comfort. Of course, there are those moments that our schedules will have a conflict due to delayed arrivals with travel and guests will check in on their own, with a four digit code, of their choice. It’s a keyless entry that will allow guests to enter the building and unit smoothly. Guests will always be able to access us for whatever they need. Any issues that arise, need to book another day or two and questions about the city or for recommendations. The condo is five blocks from the lake with its beaches, bike paths, running, and peaceful places to read the morning paper with a cup of coffee. Walk just one street to the CTA Red Line train, which connects to virtually anywhere in the city. La Fitness is across the street for your convenience. Ohare international Airport-25 mins with light traffic. 45 mins with traffic. Take Mannheim Rd N to Thouy E to Clark N to property located on the left hand side. Midway Airport-25 min with light traffic. 45 mins with traffic. I55 N to Lake shore Drive/ (Route 41)N to Sheridan Rd to Howard W to Clark S to property located on the right hand side. Red Line (L Train-CTA) 1 block East of property Bus Line (CTA)-Outside in front of the property Metra -4 blocks North or South of property Kitchen area desk is equipped with a USB electrical outlet for your convenience, as well as all three bedrooms (north walls). Both bathrooms are equipped with Bluetooth to pair your music while getting ready.

The Bright Retreat in Andersonville
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.

3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Can't Beat This 2min Walk to Wrigley!
My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Your Chicago Retreat
Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Chicago Oasis | Spa Bath, Patio & Fireplace
Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Two Bedroom w Porch in Wicker Park
Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.
Popular amenities for Chicago apartment rentals
Weekly apartment rentals

Lovely 2-bedroom close to Wrigley Field

Studio flat in the heart of Chicago's Gold Coast

Wrigleyville Inn. Historic Greystone, Free Parking
The Penthouse Gallery at OHC

Lincoln Square Gem!

NEW luxury Old Town 1-Bedroom condo

Logan Square Beauty with 2 Bedrooms W/parking

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Pet-friendly apartment rentals

Chic and Charming Vintage Condominium in Lincoln Park

Spacious 3BR • Great for Groups • Fast WiFi • Pets

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Luxuriously bright 6-bedroom duplex: The Treehouse

Picture Perfect 3Bed Steps from Train and FLW

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Cozy Downtown MICH AVE #7 | gym+rooftop

Spacious 5-BR Apt next to transit Free Parking
Apartment rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Pond View, Washer Dryer, Non Smoking Community

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $162 SGD | $166 SGD | $191 SGD | $191 SGD | $218 SGD | $231 SGD | $232 SGD | $240 SGD | $211 SGD | $215 SGD | $195 SGD | $184 SGD |
| 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 |
Destinations to explore
- Indianapolis Holiday rentals
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- Louisville Holiday rentals
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- Downtown Chicago Holiday rentals
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- Grand Rapids Holiday rentals
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- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- 875 North Michigan Avenue
- Naval Station Great Lakes
- Indiana Dunes State Park
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Frank Lloyd Wright Home and Studio
- Union Park
- Donald E Stephens Convention Center
- Washington Park Zoo
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