Holiday rental apartments in Chicago
Book unique holiday rentals, apartments, and more on Airbnb
Top-rated apartments in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
- Entire rental unit
- West Town
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!
- Entire rental unit
- Bridgeport
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
- Entire rental unit
- East Rogers Park
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).