Holiday rental apartments in Chicago

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Top-rated apartments in Chicago

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

SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #206 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

₹5,157 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
1bed/1bath !Location! Steps to South Loop 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 1br 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

₹3,570 per night
  1. Entire rental unit
  2. East Rogers Park
Short-Term Sublet Near Lake Michigan

I used to be a live-in host, but since the pandemic I host visitors while I'm away traveling, so you will have the place all to yourself! The guestroom is SUNNY & peaceful, with balcony overlooking a lush yard, set back from street = QUIET. Available for 3-6 week stays. Equivalent to a large studio apartment + kitchen + bath. 1 block from Loyola U., 3 blocks to CTA Red Line train, 4 blocks to beaches! Second floor walk-up, bed is a full-sized FUTON (firm Japanese mattress).

₹3,332 per night

Holiday rentals for every style

Get the amount of space that is right for you.

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Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park474 locals recommend
Photo of Navy Pier
Navy Pier306 locals recommend
Photo of Willis Tower
Willis Tower151 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago186 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago438 locals recommend

Houses in Chicago

  1. Private room
  2. Near West Side
Room T5
₹2,777 per night
SUPERHOST
  1. Private room
  2. McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
₹3,400 per night
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
₹2,380 per night
  1. Private room
  2. Near West Side
Room T6
₹2,777 per night
  1. Private room
  2. Little Italy
Private Room in Great Location to City
₹5,157 per night
  1. Private room
  2. South Chicago
Room H1
₹1,904 per night
SUPERHOST
  1. Private room
  2. Oak Park
Single bed room with Asian decor in family home
₹3,287 per night
  1. Private room
  2. Woodlawn
Perfect Oasis 4mins walk to University & hospital
₹4,261 per night
  1. Private room
  2. East Rogers Park
#4 Historic Chicago Home - Private Single Bedroom
₹3,808 per night
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
₹3,967 per night
  1. Entire home
  2. Humboldt Park
Elegant, Bright Flat
₹7,854 per night
  1. Private room
  2. Maywood
Room 4: The Maywood Manor (Twin Bed, 1 Guest)
₹3,434 per night

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Lincoln Square
Charming Lincoln Square Apartment Location
₹7,163 per night
  1. Entire rental unit
  2. West Town
New Spot in West Town
₹7,537 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Great location. Free parking.
₹7,933 per night
  1. Entire rental unit
  2. West Town
New Spot in West Town pt.2!
₹7,038 per night
SUPERHOST
  1. Entire rental unit
  2. Pilsen Historic District
Walk to it all in Pilsen
₹9,803 per night
  1. Entire rental unit
  2. Lincoln Park
Home in heart of Lincoln Park & Lake Sea and beach
₹5,950 per night
SUPERHOST
  1. Entire rental unit
  2. Park Ridge
Modern Garden apartment (WHOLE UNIT)
₹9,905 per night
SUPERHOST
  1. Entire rental unit
  2. Lincoln Park
Charming & Peaceful Old Town Retreat
₹7,956 per night
  1. Entire rental unit
  2. Irving Park
⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
₹6,868 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
Stylish and Cozy newly renovated Bridgeport Apt
₹7,537 per night
  1. Entire rental unit
  2. Berwyn
Lovely 1-bedroom condominium with free designated parking on premises
₹6,516 per night
SUPERHOST
  1. Entire rental unit
  2. Wicker Park
Strictly Commercial Storefront: Humboldt, Bucktown
₹9,643 per night

Apartments with kitchens

  1. Private room
  2. South Chicago
Room B7
₹1,825 per night
  1. Private room
  2. Bridgeport
Private Room A5 by Chinatown
₹2,618 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #306 at 747 Lofts
₹5,712 per night
  1. Private room
  2. Chicago
Private Bedroom near Downtown Chicago Chinatown
₹3,457 per night
SUPERHOST
  1. Private room
  2. East Garfield Park
Large bedroom near medical district and UIC
₹3,967 per night
  1. Private room
  2. Little Italy
Lovely private bedroom in Fantastic location
₹5,157 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
Bridgeport 2R Renovated 2bed/1bath Apt. MONTHLY
₹5,180 per night
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
2F Location! Steps from South Loop 1bed/1bath Apt.
₹3,967 per night
SUPERHOST
  1. Entire rental unit
  2. West Town
Cabin #103 at 747 Lofts
₹5,633 per night
  1. Entire rental unit
  2. Avondale
Great location lots of public transportation
₹6,494 per night
  1. Private room
  2. West Town
Great room with private bathroom
₹4,194 per night
SUPERHOST
  1. Private room
  2. West Town
Stylish & Ample 1PBR STAYCATION SPACE For You
₹4,228 per night
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  2. United States
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  5. Chicago