Skip to content

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.

2R Location! Steps from South Loop 2bed/2bath Apt.
SUPERHOST
Entire rental unit · 6 guests · 2 beds · 2 baths
2R Location! Steps from South Loop 2bed/2bath Apt.Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 28th Place & Canal St to map transit options Newly remodeled 2bed/2bath apt with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago & steps from all that trendy Bridgeport has to offer. Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays
Cozy Studio Apartment
Entire rental unit · 2 guests · 2 beds · 1 bath
Cozy Studio ApartmentIt’s a study that has 2 divisions: the 1st is where the kitchen and dining room are located (all newly renovated equipped) the 2nd part of the study has the space of the living room and the bedroom (1 queen size bed and a sofa bed) this is not divided by door, is a single space. It also has a full bathroom. The building has 3 levels and each level is a different apartment, the studio is on the 3rd level, there is no elevator only stairs. There is a laundry on the first level and backyard area
Lovely Studio in Great Location Chicago
Entire rental unit · 2 guests · 1 bed · 1 bath
Lovely Studio in Great Location ChicagoEnjoy the entire balanced & bright top-floor studio. W/ a fully equipped kitchen & bathroom, queen bed, walk-in closet, workspace, coffee nook, TV, printer, & washroom in the common area. Pet-friendly & suitable for long-term stays. Cooled by an a/c unit, warmed by radiators. Walking distance to local hubs, restaurants, shops, bars, grocery stores, the Metra Train & CTA transit stop. 10min drive to Lake Shore Drive, dog-friendly & public beaches, Wrigley Feild, & 15min to center of the city.

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. Chicago
m5 Self check in near downtown Chicago
SUPERHOST
  1. Private room
  2. Chicago
p09 Downtown Chicago 8 minutes away SELF CHECK IN
SUPERHOST
  1. Private room
  2. Chicago
m6 Self Check in 8 min to downtown Chicago
  1. Private room
  2. Chicago
R2 Prime New House Perfect for your stay
  1. Private room
  2. Chicago
Private room in apartment in FANTASTIC location
  1. Private room
  2. Chicago
Your Fantastic Futon! 1st Floor TV room with locks
  1. Private room
  2. Chicago
B2 - Next To Downtown Chicago - Room
SUPERHOST
  1. Private room
  2. Chicago
p01 Downtown Chicago 8 minutes away New Queen Bed
  1. Private room
  2. Chicago
5min walk to UnivOfChgo. MODERN Luxe
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
SUPERHOST
  1. Private room
  2. Chicago
Room T3
  1. Entire residential home
  2. Franklin Park
Welcoming 1 Bedroom in quiet area, Free parking

Pet-friendly apartments

  1. Entire rental unit
  2. Chicago
New Spot in West Town pt.2!
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
SUPERHOST
  1. Entire rental unit
  2. Chicago
Stylish and Cozy newly renovated Bridgeport Apt
  1. Entire rental unit
  2. Chicago
Stylish mid-century modern apartment
  1. Private room
  2. Chicago
Simple and Convenient
  1. Entire rental unit
  2. Chicago
Lovely 2-bedroom rental unit
  1. Entire rental unit
  2. Chicago
The Secret Stache
SUPERHOST
  1. Entire rental unit
  2. Chicago
The Hobbit Hole
  1. Entire rental unit
  2. Chicago
Urban Farm Fun! Walk to Metra/CTA
  1. Entire rental unit
  2. Chicago
LUXURY 2BR APARTMENT | Wi-Fi | FREE PARKING|
SUPERHOST
  1. Entire rental unit
  2. Chicago
Relaxed Bucktown/Wicker Park 1B Apt
SUPERHOST
  1. Entire rental unit
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨

Apartments with WiFi

  1. Entire rental unit
  2. Chicago
1 Bedroom Apartment by McCormick Place & Chinatown
  1. Entire rental unit
  2. Chicago
Cute Designer Touch Minimal Loft,Blue Line
  1. Entire rental unit
  2. Chicago
Deluxe Modern 2BR Apt 4min walk to UofC & Hospital
SUPERHOST
  1. Entire rental unit
  2. Chicago
1bed/1bath !Location! Steps to South Loop Apt
  1. Private room
  2. Chicago
Frida 2720 (2F)
SUPERHOST
  1. Private room
  2. Chicago
Spectacular Downtown High Rise Extraordinary view
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat
SUPERHOST
  1. Entire rental unit
  2. Chicago
Private Studio Apt in the Heart of Wicker Park!
  1. Private room
  2. Chicago
Stylish, Shared Apartment for the Perfect Get Away
SUPERHOST
  1. Entire rental unit
  2. Chicago
Pilsen Tranquil Renovated 2bed/1bath Apt MONTHLY
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
SUPERHOST
  1. Entire rental unit
  2. Chicago
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!