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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.

Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOST
Entire rental unit · 5 guests · 2 beds · 1 bath

Bright family-friendly Lincoln Square 2-bed 1-bathLight-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOST
Entire rental unit · 2 guests · 2 beds · 1 bath

Basement Studio w/Free St. Parking, Humboldt ParkLocated 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.

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

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge, portable AC IN BR, Blackout curtains, 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 HDMI hookup. Iron/board, closet w/ hangers, sharper image radio/speakers/cd player, basic office supplies. Printer in LR. Free parking with permits (ask).

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
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Popular apartment amenities in Chicago

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

Houses in Chicago

SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
G$10,648 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
G$23,896 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
G$12,980 per night
  1. Entire residential home
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
G$23,867 per night
  1. Private room
  2. Chicago
m4- Cleanest & Newest place near downtown chicago
G$7,328 per night
SUPERHOST
  1. Private room
  2. Chicago
Sunny full floor (4+) & gym!
G$9,182 per night
SUPERHOST
  1. Private room
  2. Chicago
p06- Downtown Chicago 8 minutes away New Queen Bed
G$8,554 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
G$8,883 per night
PLUS
  1. Private room
  2. Elmhurst
Chic Oasis near Downtown Chicago
G$18,394 per night
SUPERHOST
  1. Private room
  2. Chicago
Huge Victorian near Loyola, Lake #3
G$14,446 per night
  1. Private room
  2. Chicago
m1- 9 min to downtown Chicago, 5min to Chinatown
G$8,374 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
G$6,310 per night

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Forest Park
Cute 1 bedroom near Blue line
G$14,716 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Large High-Class Apt Near Beach w/ Free Parking!
G$36,548 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
G$18,124 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
G$17,586 per night
  1. Entire rental unit
  2. Chicago
Wicker Park Charmer
G$32,689 per night
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
G$19,022 per night
PLUS
  1. Entire rental unit
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
G$31,762 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Discover Chicago from a Modern Apartment
G$38,492 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy and Comfy 1BR Apartment in Logan Square!
G$28,173 per night
  1. Entire rental unit
  2. Chicago
Truly Comfy, Elegant Home w/ Garage by Wrigley/CTA
G$23,000 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
G$36,638 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming Lincoln Square Apartment Location
G$16,240 per night

Apartments with WiFi

  1. Entire rental unit
  2. Chicago
East Village Oasis
G$21,744 per night
  1. Entire rental unit
  2. Chicago
Beautifully Renovated, Walking distance to Lake!
G$17,915 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
G$22,253 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Spacious, light-drenched studio-private entrance!
G$17,197 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Logan Square/Avondale Chic Retreat W/Peloton Bike
G$21,922 per night
PLUS
  1. Entire rental unit
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
G$20,636 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
G$10,767 per night
PLUS
  1. Entire rental unit
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
G$19,142 per night
  1. Entire rental unit
  2. Chicago
Sophisticated & updated, walking distance to Lake!
G$19,410 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Entire City Apartment One block to Train Park Free
G$16,479 per night
  1. Entire rental unit
  2. Cicero
Mid-Cen-Mod Rustic Studio.
G$16,569 per night
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat
G$6,760 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:G$5,653 / 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:G$6,281 / person
  • MUST HAVE CHICAGO PHOTOS- OUTDOORS
    IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT We’ll start with a talk in Chicago Cultural Center by the bull and get to know each other. If it’s a small group during the experience, we will walk together around various locations but everybody has their own personal time with me while I photoshoot. Together we’ll discover the places and pictures that YOU NEED TO HAVE from Chicago , from the magical MILLENNIUM PARK, THE BEAN , CHICAGO THEATER AND RIVER WALK while I capture moments of you and/or any friends or your partner to take home. Feel free to tell me your ideas or preferences Other things to note THIS IS A SMALL GROUP EXPERIENCE AND EVERYBODY HAS THEIR OWN TIME (YOU CAN ALSO HAVE PRIVATE PHOTO SHOOTINGS IN CASE THAT YOU NEEED SOMETHING MORE PRIVATE) Please feel free to visit more of my work at www.carlacarrascoocampo.com also on IG at carrascoocampo
    From Price:G$18,633 / person
  • All-Weather Architecture & History Trek
    I pack lots of sights, sounds and experience 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!). We'll 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 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:G$6,072 / person
  • Lifestyle City Photo Shoot/Tour
    Standing in front of a camera can be quite intimidating. With experience both in front of and behind the lens, I will always do my best to help you capture the best natural travel photos in the city of Chicago. Worried about how you'll look? Don't be! I will always show you the photos before moving forward. During this experience I will not only help you receive beautiful photos but I will also try to teach you insight about modeling and photography. This experience will be ideal for individuals who are looking for a city tour but would also love to capture some scenic travel and portrait images. I love to build positive connections with others, so this is great for someone who wants to be more engaged and collaborative with their guide. I will be using a Sony DSLR to capture your candid and lifestyle moments. This includes both portraits and full body shots. If you would like to learn more about the editing process or a photographer's guides, let me know and I am more than happy to share my knowledge. You will receive 8 edited images and all unedited photos (usually 200+). Editing does not include body manipulation, but can be requested for an additional charge. If you do not see a time that works for you on the calendar, please send me a message! I do accept large parties! Please note that I cannot guarantee a private session unless you booked as a private session.
    From Price:G$18,633 / person

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