Skip to content
Sign up
Log in
Vacation rental apartments in Chicago

Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated apartments in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Edgewater, private, charming coach house 1 ( of 2)
SUPERHOST
Entire apartment · 3 guests · 1 bed · 1 bath

Edgewater, private, charming coach house 1 ( of 2)Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

Casa de Sueño/Private Bathroom/Near Train/Loyola
Private room · 2 guests · 2 beds · 1 private bath

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge flat screen TV with Apple TV with free Netflix, you can Stream movies/shows through your Apple device or use one of these converter apps to stream from android: https://letsview.com/mirror-android-to-apple-tv.html Also has an Amazon Firestick and HDMI hookup. Iron/board, closet w/ hangers, sharper image radio/speakers/cd player, basic office supplies. Printer in LR. Free parking with permits (ask).

Great location. Free parking.  One night available
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Great location. Free parking. One night availableGreat location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
  • Guesthouses

Popular apartment amenities in Chicago

  • Wifi
  • Kitchen
  • Air conditioning
  • Free parking
  • Heating

Houses in Chicago

SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu

Catmandu bedroom #1: Private en suite with comfy Queen size bed and a loveseat sitting area that pulls out to a single size bed if needed.

G$10,463 per night
SUPERHOST
  1. Entire house
  2. Chicago
Private Andersonville Guest Suite

Lovely private guest suite in beautiful Andersonville neighborhood. Enter through the back garden to relax in your city oasis; with spa bathroom, cozy living room, and queen bed. Have coffee on the patio in the summer and take easy walks to train, beach, shopping and dining.

G$24,603 per night
SUPERHOST
  1. Private room
  2. Chicago
Logan Square Vintage Deluxe Private Suite & Bath

A private vintage haven - bedroom, bath and living space - in the heart of Logan Square. Surrounded by great shopping, food, cafes and bars, witheasy travel to downtown. We follow the Airbnb guidelines for enhanced cleaning, to ensure a safe visit for all. Kitschy and cool, cozy and comfortable - a walk up, second floor, private suite in a classic Chicago Victorian frame house on a quiet neighborhood street. Free street parking. A small, separate entry space that's all yours. Dog friendly!

G$14,649 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!

Experience a bright contemporary style home. Enjoying private access to a cozy bedroom and beautiful bathroom in our Andersonville home. The first-floor bedroom is steps away from the bathroom with an ultra-relaxing rainfall shower. New furnishings and amenities in the well-appointed, bedroom include a full bed/mattress, TV/Netflix, fridge, ample closet space, central heat/air, and heated floors. Walking distance from public transportation to tourist destinations and great restaurants and shops.

G$10,524 per night
SUPERHOST
  1. Private room
  2. Chicago
Entire floor urban retreat private guest suite

Our private urban retreat with vaulted ceilings, features a private master bathroom and sitting room that takes up the entire floor. Located in Andersonville, we are steps from the train, beaches, great dining and shopping. Walking distance to the Avalon Ballroom and Rivera Theater. Close to Wrigley Field and the Cubs. It's a quick train ride downtown or to Evanston. Due to the coronavirus, we’re taking extra steps to clean and sanitize!

G$12,945 per night
  1. Entire house
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. We take the pandemic very seriously, and follow the EPA/CDC protocol. We thoroughly prepare for your stay with intensive cleaning and disinfecting.

G$20,987 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Private bedroom A in a quiet Chicago suburb.

Stay in the Lincoln Room across a beautiful park on a quiet non-smoking home in a safe suburb. Airbnb Superhost. Near to I-55, I-294, LaGrange Rd and Archer for 25 minutes drive to downtown. Free driveway parking. Sunny bedroom with Queen-size bed for 2 people max. This is 1 of 3 bedrooms available. Natural light bathroom with a sky window is shared with another Airbnb room. Good for business, solo, or couples (gay or straight) travelers. NO discrimination allowed.

G$7,324 per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago

Recently renovated, enjoy the comfort of staying on a brand new home with everything brand new. Brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix included, expensive luxury mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more! Convenient location close to downtown Chicago, Chinatown, White Sox, Pilsen, South Loop & McCormick Convention Center.

G$7,354 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2

Catmandu bedroom #2: Private room with comfy queen size bed and a loveseat sitting area that pulls out to a single size bed if needed. Bedroom is in close proximity to bath (across the hall). If this room is unavailable on the dates you would like, you have more then 3 guests and need more room, or simply just interested in seeing what else I offer, check out catmandu bedroom #1! https://www.airbnb.com/rooms/30446996

G$8,371 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer

single family home with bedroom (second floor) available with shared bath. Room is for single occupancy only, no exceptions. See our other listing for private room with single bed.

G$6,069 per night
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking

My century old home holds distinctive characteristics such as an open concept plan, earth-tone color palette, unique natural light design, a newly remodeled bathroom; and free parking on site. With easy access to public transportation, either to Northwestern, or to Loyola University, walking distance from Presence St. Francis Hospital. My place offers a quiet place for scholars, PhD and postdoc students, or those looking for a space to relax.

G$7,385 per night
  1. Entire house
  2. Chicago
Newly Renovated 2br, 1 ba- Logan Square

2br, 1 bath, flat in one of Chicago’s favorite neighborhoods, Logan Square. Quiet, tree lined streets, centrally located with flexible transportation. 15 min from downtown., Divy Bike rental, bus lines, Blue Line Train. All of the amenities needed for families, singles, couples; short or long stays. -Private Flat -Personal door code -Free WiFi -Ample street parking -Washer/Dryer -Professional Cleaning/Disinfection Convenience of owner onsite. We're here if you need anything!

G$17,788 per night

Pet-friendly apartments

SUPERHOST
  1. Entire apartment
  2. Chicago
Susie's Sanctuary- Pet friendly +parking

Large 1000 sq foot, 1 bedroom apartment in hip Avondale. Roomy kitchen with breakfast bar, office area. WIFI and smart TV for streaming. Cozy bedroom with a queen bed and closet. Chef's kitchen and dining area. Pet fee $10 per pet/day

G$24,903 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks

Newly remodeled one bedroom plus queen sleeper sofa in historic Ravenswood Manor. This unit is on the ground floor of an owner-occupied three-flat on a beautiful tree-lined street with plenty of parking. Close to Brown Line - Francisco Stop - and lots of neighborhood parks. Close to Rockwell and Lincoln Square shopping and restaurants, and next to Albany Park, one of Chicago's most diverse areas. New fixtures, furniture, appliances, free shared laundry, access to backyard upon request.

G$14,291 per night
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos

Sunny, quiet first floor 2 bedroom apartment in owner occupied 4-Flat apartment building. It is located in the Southwest corner of Chicago’s Cook County. [Note: long term stays are available.] The building's eastern view overlooks the southern suburbs of Chicago Ridge, Oak Lawn and Bridgeview.

G$18,834 per night
PLUS
  1. Entire apartment
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard

Soak in the private outdoor hot tub in the leafy, fenced-in yard outside this spacious studio. The home boasts high ceilings with exposed silver ducting and eclectic decorations, including cow print furniture, and an intricately carved bathroom door. While the decor is eclectic, the king-size bed sets the standard for comfort. The Checkerboard Studio is perfect for a cozy getaway and offers intimacy, but with enough space to move. Functional kitchen is well supplied and easily navigated. If the outdoor hot tub doesn't appease your need for bubbles, the jetted tub and shower stand ready.

G$23,607 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Discover Chicago from a Modern Apartment

Stretch out on a plush sectional sofa in the living room of this airy 3-bedroom/1-bath modern apartment with tall ceilings. Offering contemporary fixtures and fittings, plus a showcase fitted kitchen with classy dark wood cabinetry, the interior conjures a tasteful, relaxing ambience. Amenities including cable tv, wifi, and one reserved parking spot. This home perfect for families!

G$26,129 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Private Beachfront Retreat includes parking

Patio Space facing Lake is under construction through May 5th Apartment pictures are 100% accurate Less than a 10min drive to Downtown Evanston and Loyola University. Fast Internet and includes a phone charging station with cables. Onsite Parking Spot In-Unit washer/dryer, iron board with iron & safe Drip coffee, tea, condiments, and snacks. Stocked Chef's Kitchen with condiments Internet TV includes Amazon Prime & Netflix Wireless Sono Speakers

G$56,353 per night
  1. Entire apartment
  2. Chicago
Cozy & Modern | Near Humboldt Park, two Queen, Pkg

Step into the comfort of this cozy 2 BR apt with outstanding facilities, mere minutes from the historic Humboldt Park. It promises an urban retreat at a great location, allowing you to explore numerous attractions, landmarks, and places of interest. Chicago living at its best! Contemporary design and rich amenity list will satisfy your every need. ✔ 2 Comfy BRs (2 queen Beds) ✔ Open Plan Living ✔ Fully Equipped Kitchen ✔ Private Outdoor Deck ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

G$20,927 per night
  1. Entire apartment
  2. Chicago
MidCentury Logan Square / Bucktown Loft

Large Studio Loft with separate sleeping area, living, dining, and kitchen in a historic building. Huge windows overlook Armitage Avenue. 16 Foot Ceilings and high-end finishes. Very easy access in/out. Located above Margie's Candies & Snakes and Lattes, both great eateries. Great coffee shop is right downstairs as well. Just 50 feet from the Western Blue Line stop with easy access to O'Hare, Logan Square, Wicker Park, Bucktown, and the Loop.

G$18,625 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
❤️ Low Prices! Stylish 2BR Condo in Logan Square!

Welcome to Chicago! Home of World Series Champs Cubs. Our 2-bedroom/1 bathroom condo is perfect for getaway to Chicago. It's professionally designed with modern furniture that gives welcome feeling! We're located in Trendy Logan Square Designated parking spot is NOT available, but there is plenty of street parking available.-The entire condo is for your own use.

G$22,871 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Entire 1st Floor Apt near O'Hare/ORD & Blue Line

You’ll love my place because of privacy, comfort, first floor convenient access (no stairs), no clutter, the ambiance, the neighborhood, free on-street parking and your host (conveniently living in a separate apartment on the second floor). My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

G$19,581 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is small historic district of Chicago filled with historic architecture. Access the apartment via smart lock, the apartment includes everything you need for a comfortable stay including Queen sized bed, full kitchen, high speed internet, Samsung smart tv, hardwood floors, modern bathroom, in-unit washer & dryer, and free garage parking.

G$20,537 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Relaxed Bucktown/Wicker Park 1B Apt

One bedroom, pet friendly, apartment provides a temporary retreat with its cozy clean comfortable charm. Great reviews! Loaded with amenities. Steps from Chicago's best Restaurants, boutiques, coffee shops, nightlife.

G$11,420 per night

Apartments with WiFi

SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

G$16,651 per night
  1. Private room
  2. Chicago
Hattie’s House

My space is very accessible to public transportation ( walking distance to 3 bus lines) also a neighborhood grocery store 1 Blk away ( for essentials & alcohol & ATM) for eating establishment also close corner block has a French restaurant (Jean-Marie) , bakery (Spinning J) , Bar restaurant (Rootstock Wine & Beer) and Pizza bar (Dante’s ) great breakfast diner “Flying Saucer”

G$7,354 per night
PLUS
  1. Entire apartment
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park

Whip up tasty home-cooked meals in this chic, modern condo. Though cozy in size, the open-plan layout maximizes on space. You’ll have everything you need for the duration of your stay including a patio and great local attractions.

G$20,029 per night
PLUS
  1. Entire apartment
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment

Keep updated on work demands at a vintage-style wooden desk in the working corner of this gorgeous studio apartment. The combination of metals, velvet and wood in the interior make this a beautiful apartment and a contemporary dream. Please note that this unit is located above a late night bar, which may add to the charm of it for some but may also pose to be a noise nuisance for light sleepers. We encourage you to read the reviews of past guests to make an informed decision.

G$14,050 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park

Located in Humboldt Park, 6 miles from downtown, this basement studio is perfect for a stay in Chicago. We are located on a strip with approximately 11 houses and no houses across. There is a lot of Park area. At night it's a quiet neighborhood. We are located half a block away from the bus to Navy Pier, approx. 45 minutes to get to Navy Pier. There is free street parking available with NO parking permit required. There is a pool (only in summer) and park access half a block away.

G$12,108 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Edgewater, private, charming coach house 2 ( of 2)

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

G$18,909 per night
SUPERHOST
  1. Entire apartment
  2. Oak Park
Cosmopolitan nest in Oak Parks North Side

Whether visiting Oak Park's historic district or exploring the Windy City for the renowned museums and its nightlife, we welcome you into our home. You are guaranteed a peaceful stay in your own apartment with private entrance on the first floor in our single family home. We are a professional family who maintain a quiet residence. CTA public transportation just steps away.

G$10,882 per night
  1. Entire apartment
  2. Chicago
Heart of Bucktown Private Retreat

This completely updated apartment, including a brand new, large bathroom with tub and separate shower, sits right in the middle Chicago's posh and trendy Bucktown. The rest of the building was completely renovated with Nest lock system. The giant bedroom comes with an Ethan Allen queen size bed, a Pottery Barn chest of drawers and a large closet. Free laundry right downstairs exclusively for this unit and a bedroom that overlooks the landscaped private yard makes this the perfect Chicago stay!

G$14,649 per night
  1. Entire apartment
  2. Chicago
Spacious 1 Bedroom Oasis in Center of Wicker Park

This 1 bed/1bath garden unit in Wicker Park, one of the trendiest neighborhoods of Chicago, is in a beautiful all brick fully renovated 3unit building. Steps away from great restaurants, coffee shops, two short blocks to the blue line train. Easy access from the airport and rest of city. SUPER fast wifi, a great workspace, fully stocked kitchen, washer/dryer in unit, 2 smart tvs (with Netflix, HBO, and tons of other streaming services). Parking available upon request. List goes on and on!!

G$16,383 per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary

This cozy 2 bedroom apartment is bathed with bright warm light in every room. It feels like your own private sanctuary. A true getaway! The location is great. Lake Michigan is only about ten minutes by bike or five minutes by car. Loyola university is just up the street. The red line train is only about six blocks walking distance. Andersonville, which is a great little neighborhood with restaurants, coffee shops and boutiques is just a few minutes drive away. Free street parking available.

G$17,011 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious Apartment minutes from Downtown/McCormick

Perfect for your trip! This beautifully remodeled Chicago Bronzeville apartment is located minutes from McCormick, Soldier Field, University of Chicago, and 15 minutes from downtown, Magnificent Mile, Navy Pier, beaches, Grant Park, the Bean, restaurants, shopping and more! The bus is a half block away, the train is 2 blocks away. This garden unit apartment has 2 bedrooms, 1 bathroom, a fully equipped kitchen, living room, washer/dryer, cable TV, WiFi and abundant street parking!

G$12,407 per night
  1. Entire apartment
  2. Chicago
Cool but Comfy First Floor in hoppin' Logan Square

This Logan Square whole First Floor, 2 Bed/1 Bath apt is a cool, and comfy unit in a host-occupied building. (I live upstairs, so I can help with any questions.) The bath has been updated and the kitchen is fully equipped. There’s an awesome garden with an available grill out back in case you don't feel like strolling through the area to one of the great restaurants, bars or parks. Lots happens in the neighborhood, but here, you can still feel like you've gotten away. Great location!

G$17,997 per night

Nearby destinations