Explore the area
Chicago vacation rentals & nearby suburbs
Published · Updated
Find a place for your Chicago visit, with options in the city and nearby suburbs. Compare the city shown on each property before choosing the setting that fits your plans.
40 stays in Chicago · 46 in the Chicago area · including 13 private rooms
Which Chicago vacation rental is right for my group?
It depends on how many of you are coming and what you need. For 8 or more guests, 16 of the 46 homes on this page are big enough, and the largest sleeps 26. Couples and small families can choose from 21 homes that sleep 4 or fewer. For a specific need, compare the monthly stays (33) and pet-friendly stays (32) lists below. The neighbourhoods with the most homes are Near South Side (13) and Irving Park (6). Counts as of November 2, 2026.
Choose the location that fits your trip
Chicago searches include surrounding communities such as Lombard and Elmwood Park. A suburban home may offer a different layout or capacity from a city apartment. Review each home's neighbourhood, room details and map before booking; travel times depend on your plans and transportation.
Homes in Chicago and the surrounding area
46 properties in the current area catalog. Select dates and guests to check availability and the total for your stay.
More homes in the Chicago area
- Private Workspace, Coffee Bar & Near Transit · Belmont Cragin · Chicago, Illinois
- Coffee Station & Backyard w/ Grill · Belmont Cragin · Chicago, Illinois
- Traveler's Favorite & Modern and Clean · Belmont Cragin · Chicago, Illinois
- Home with Theater, Game Room & Gym · Chicago, Illinois
- Near Lakefront & Red Line, Workspace & Apt · Rogers Park · Chicago, Illinois
- Walk to the Beach & Private Office · Rogers Park · Chicago, Illinois
- Game Room, Gym & Theater · Portage Park · Chicago, Illinois
- Arcade, Theater, Gym & Office · Portage Park · Chicago, Illinois
- Private Gym and Workspace & in Quiet Location · Dunning · Chicago, Illinois
- Gym, Workspace, Near O’Hare & New Modern · Dunning · Chicago, Illinois
- Near O'Hare, Office & Coffee Bar · O'Hare · Chicago, Illinois
- Newly Furnished Modern Apt & Near O'Hare · O'Hare · Chicago, Illinois
- Modern Condo & Safe Chicago Stay Near O’Hare · O'Hare · Chicago, Illinois
- Remodeled Safe Chicago Condo · O'Hare · Chicago, Illinois
- Near O'Hare, Balcony & Workspace · O'Hare · Chicago, Illinois
- Modern w/ Workspace near O'Hare · O'Hare · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Downtown with Budget-Friendly Room & Free Coffee · Near South Side · Chicago, Illinois
- Near Zoo & Beach & Reading Nook + Parking · Lincoln Park · Chicago, Illinois
- Near Lake & Museum, Modern & Game Area · South Shore · Chicago, Illinois
- Top Rated Condo · Elmwood Park, Illinois
- King Bed Studio, 60" HDTV, Safe & Close to Metra · Elmwood Park, Illinois
- Cozy Home · Lombard, Illinois
Neighbourhoods in Chicago
Staying with a group?
14 homes in this area list capacity for at least eight guests. Check bedrooms, beds, occupancy limits and house rules on each property before booking.
Group stays in ChicagoStaying while your home is repaired?
We list furnished entire homes for people displaced by a fire, water damage or another loss, with an itemized quote on request.
Insurance housing in ChicagoBefore you book
Does a Chicago search include the suburbs?
Yes. Chicago searches include nearby areas, including Lombard and Elmwood Park. Every property card shows its own city so you can compare locations before selecting dates.
Which Chicago vacation homes sleep 12 or more guests?
8 of the 46 homes on this page are in Chicago itself and sleep 12 or more; the largest sleeps 26. Group stays in Chicago shows larger homes together. Check each home's bedroom and bed layout before you book.
Can I cancel?
For stays booked more than 30 days ahead, you can choose a refundable rate: free cancellation until a date 30 days before check-in. If you cancel by then, everything you paid is refunded automatically except the card processing fee, which is non-refundable. It costs 8% more on the nightly subtotal, and the booking form shows the total for each option. Stays starting within 30 days are offered at the non-refundable rate only. The standard rate is non-refundable.
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