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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.

Mid-Century Modern Charm. Close to Chicago.
Entire rental unit · 4 guests · 3 beds · 1 bath

Mid-Century Modern Charm. Close to Chicago.Step back in time a bit with our charming 2nd floor walk-up in a quiet suburb. Newly remodeled but with a vintage, welcoming vibe. A short walk to the train or a 20-minute drive to downtown Chicago. We live downstairs and are happy to say hi, or happy to leave you in peace, whichever you prefer. Free Parking. Great wifi. 3-season back porch. Feel free to relax in our welcoming back yard. Record Player (Real Vinyl!)

Stunning Retro Apartment in Andersonville
PLUS
Entire rental unit · 4 guests · 2 beds · 1 bath

Stunning Retro Apartment in AndersonvilleEscape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full of natural light, the apartment features modern decor and an arty ambiance, making it playful and fun to stay. Free street parking.

Cozy and Stylish Studio with Free Parking in Irving Park
PLUS
Entire rental unit · 2 guests · 1 bed · 1 bath

Cozy and Stylish Studio with Free Parking in Irving ParkWhip 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.

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 on premises
  • Heating

Houses in Chicago

  1. Private room
  2. Chicago
m5- Self check in near downtown Chicago
ﺩ.ﺇ132 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
ﺩ.ﺇ151 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
ﺩ.ﺇ186 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
ﺩ.ﺇ392 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
ﺩ.ﺇ232 per night
SUPERHOST
  1. Entire residential home
  2. Chicago
Quiet & Cozy Garden Unit with Private Entrance
ﺩ.ﺇ214 per night
SUPERHOST
  1. Private room
  2. Chicago
McCormick001, GrantPark, Chinatown,UC, freeparking
ﺩ.ﺇ281 per night
SUPERHOST
  1. Private room
  2. Chicago
Entire floor urban retreat private guest suite
ﺩ.ﺇ219 per night
  1. Private room
  2. Chicago
m6- Self Check in 8 min to downtown Chicago
ﺩ.ﺇ149 per night
PLUS
  1. Entire residential home
  2. Chicago
Feel at Home in Chicago, with Parking, Steps from Evanston
ﺩ.ﺇ493 per night
  1. Entire residential home
  2. Elmhurst
Elmhurst NEW - Super Clean Modern Farmhouse!
ﺩ.ﺇ978 per night
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking
ﺩ.ﺇ129 per night

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
ﺩ.ﺇ392 per night
SUPERHOST
  1. Private room
  2. Chicago
Casa de Sueño/Private Bathroom/Near Train/Loyola🌙😴
ﺩ.ﺇ168 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
ﺩ.ﺇ317 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
ﺩ.ﺇ643 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
ﺩ.ﺇ415 per night
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
ﺩ.ﺇ336 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
CASA NEWPORT
ﺩ.ﺇ557 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ukrainian Village Garden Retreat
ﺩ.ﺇ494 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
♥Modern & Chic 3BR | Fireplace+Netflix+Parking♥
ﺩ.ﺇ534 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy Private Coach House
ﺩ.ﺇ302 per night
  1. Entire rental unit
  2. Chicago
Angie’s Nest
ﺩ.ﺇ470 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Garden Luxury condo in historic greystone.
ﺩ.ﺇ731 per night

Apartments with WiFi

PLUS
  1. Entire rental unit
  2. Chicago
Garden Retreat in a Tranquil Location in West Lakeview
ﺩ.ﺇ425 per night
  1. Entire rental unit
  2. Chicago
1 Bedroom Apartment by McCormick Place & Chinatown
ﺩ.ﺇ219 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
ﺩ.ﺇ334 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Wicker★Park Blue Line Subway@Division East★Village
ﺩ.ﺇ296 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Logan Square/Avondale Chic Retreat W/Peloton Bike
ﺩ.ﺇ348 per night
PLUS
  1. Entire rental unit
  2. Chicago
Redesigned Lower Level Studio in Historic Building
ﺩ.ﺇ478 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
ﺩ.ﺇ158 per night
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat
ﺩ.ﺇ109 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Tiny Studio Apartment 94 Walk Score
ﺩ.ﺇ239 per night
  1. Entire rental unit
  2. Chicago
Calming Edgewater Glen Sanctuary
ﺩ.ﺇ367 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
ﺩ.ﺇ213 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
CLEAN Cozy Vintage Chicago Apartment near Downtown
ﺩ.ﺇ301 per night

Top-rated things to do in Chicago

Unique activities hosted by local experts vetted for quality

  • Gangsters and Ghosts Tours
    One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
    From Price:ﺩ.ﺇ100 / person
  • Chicago's Underground Donut Tour
    On this tour, you'll join me as we explore the city and food culture through the medium of donuts. You'll learn about the history of Chicago, each donut location, how they fit into the larger food scene, as well as try some amazing donuts. We start from Doughnut Vault where we try some of the best donuts you've had in your life. Next we'll stop by Firecakes donuts to try a few of their seasonal flavors. Followed up with Stans Donuts near Michigan avenue and finally, we end at Do-Rite Donuts where they have both delicious donuts and fried chicken (if you want to get nuts at the end of the tour). We look forward to seeing you soon! Other things to note Let us know ahead of time if you have any dietary restrictions (gluten free, vegan, peanut allergy, etc.)
    From Price:ﺩ.ﺇ111 / person
  • All-Weather Architecture & History Trek
    I pack lots of sights, sounds and experiences on this tour so put on your walking shoes! We first meet in a sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). Learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while digesting some of our city's most prominent sights. Using some of the Loop's buildings and sculptures, we'll get rare, unique views and traverse the city like a local. If you're curious about Prohibition-era gangster lore or our speakeasy past, we can cover that too. Be prepared for indoor and outdoor walking as our trek will take us outside, especially during warmer weather. Please let me know if you have any allergies or food sensitivities, as we’ll be stopping for an authentic Chicago snack that's been around for more than a century. Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together! COVID-19 UPDATE: We're spending more time outside as there is PLENTY to see & keeping the groups small so we can practice safe social distancing.
    From Price:ﺩ.ﺇ107 / person
  • Explore Dazzling Architecture Interiors
    Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
    From Price:ﺩ.ﺇ111 / person
  • Lincoln Park/Lakeview Photoshoot!
    Do you want some candid pictures of you and your family on your summer vacation? Or perhaps you are looking for some cute new pictures with your significant other or best friend? Or maybe you just want some cool artsy pictures by yourself for your instagram? ...No matter what your occasion is I can capture that special moment for you! I will be photographing my guests at the Lincoln Park Conservatory & then down by a scenic city view on the Lakefront (in an area only locals know about).. I want to offer an experience for tourists that can document the experience of their getaway, while offering them something off the beaten path in this wonderful city! Other things to note Wear attire that you feel comfortable & confident in!
    From Price:ﺩ.ﺇ313 / person

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