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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.

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).

Great location. Free parking.  One night available
SUPERHOST
Entire rental unit · 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 on premises
  • Heating

Houses in Chicago

SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
  1. Entire residential home
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
SUPERHOST
  1. Private room
  2. Chicago
Sunny full floor (4+) & gym!
SUPERHOST
  1. Private room
  2. Chicago
p06- Downtown Chicago 8 minutes away New Queen Bed
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
SUPERHOST
  1. Private room
  2. Chicago
Huge Victorian near Loyola, Lake #3
PLUS
  1. Private room
  2. Elmhurst
Chic Oasis near Downtown Chicago
  1. Private room
  2. Chicago
m1- 9 min to downtown Chicago, 5min to Chinatown
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
PLUS
  1. Entire residential home
  2. Chicago
Feel at Home in Chicago, with Parking, Steps from Evanston

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Forest Park
Cute 1 bedroom near Blue line
SUPERHOST
  1. Entire rental unit
  2. Chicago
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOST
  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
  1. Entire rental unit
  2. Chicago
New Listing! Modern light filled apt close to DT!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
PLUS
  1. Entire rental unit
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
SUPERHOST
  1. Entire rental unit
  2. Chicago
Discover Chicago from a Modern Apartment
SUPERHOST
  1. Entire rental unit
  2. Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy and Comfy 1BR Apartment in Logan Square!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming Lincoln Square Apartment Location

Apartments with WiFi

PLUS
  1. Entire rental unit
  2. Chicago
Stunning Retro Apartment in Andersonville
  1. Entire rental unit
  2. Chicago
Beautifully Renovated, Walking distance to Lake!
SUPERHOST
  1. Entire rental unit
  2. Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
SUPERHOST
  1. Entire rental unit
  2. Chicago
Spacious, light-drenched studio-private entrance!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Logan Square/Avondale Chic Retreat W/Peloton Bike
PLUS
  1. Entire rental unit
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
PLUS
  1. Entire rental unit
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOST
  1. Entire rental unit
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOST
  1. Entire rental unit
  2. Chicago
Entire City Apartment One block to Train Park Free
  1. Entire rental unit
  2. Chicago
Clean & Renovated, Walking to distance to lake!
  1. Entire rental unit
  2. Cicero
Mid-Cen-Mod Rustic Studio.
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat

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:€23 / 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:€26 / 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:€75 / person
  • Shop Hidden Thrift Stores
    A great thrifting trip is all about the thrill of the hunt! Finding the great scores happens early, so we'll get energized with coffee or a snack at our meet-up point, then walk or take public transit to 3-4 of the best thrifting spots in Chicago and spend ABOUT an hour at each. Each spot is at top of my list when I'm looking for my next favorite item. Not only is thrift shopping great for your wallet, but it's sustainable for the environment! This tour is intimate and interactive so get ready to chat and thrift with folks who's tastes and lifestyles are completely different from your own. Making new friends is encouraged! Locals are welcome: this tour ain’t only for tourists! This is not a vintage tour. A successful thrift adventure requires vision to see the unique possibilities in an every day item - the right styling can transform something you'd initially pass up. That's where we come in! We are available to help scour the racks, give advice on how that leather jacket or platform shoes look or happy to let you do your own thing! As your experienced tour guide, I will make sure you go with a new favorite item. *If you are interested specifically in vintage finds, please check out my "Hidden Vintage & Boutique" tour on AirBnB! Other things to note Please reach out to me with questions! If you don’t arrive by CTA, I can help you snag a pass at the station together before we begin the tour.
    From Price:€21 / 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:€75 / person

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