Vacation rentals in Chicago
A big American city that rents like a neighborhood one: full apartments and condos in the Loop, River North, Lincoln Park, and the West Loop, with Lake Michigan on one side and 77 neighborhoods on the other.
Best time to book
Late May through September for lakefront weather, patios, and festivals, with September and early October the sweet spot for mild days and lower rates. December brings holiday markets and Michigan Avenue lights; January and February are genuinely cold.
Common rental types
Downtown apartments · High-rise condos · Neighborhood two-flats · Loft apartments · Family apartments · Extended-stay condos
Getting there
Fly into O'Hare (ORD) or Midway (MDW); the Blue Line and Orange Line connect both to downtown for the price of a transit fare. Amtrak arrives at Union Station. You do not need a car — CTA trains and buses, plus rideshare, cover almost every visit, and downtown parking is expensive.
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Vacation rentals in Chicago
Listings for Chicago are coming soon
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Where to stay in Chicago
The Loop
The historic core: Millennium Park, the Art Institute, the theatre district, and the elevated tracks overhead. Quiet at night, unbeatable for first-time sightseeing.
River North
Galleries, steakhouses, and the highest concentration of hotel-style condo rentals. Walkable to the Riverwalk and Michigan Avenue.
Magnificent Mile & Streeterville
Michigan Avenue shopping, Navy Pier, Ohio Street Beach, and lake views from high floors.
Gold Coast
Historic mansions, Oak Street Beach, and tree-lined streets between downtown and Lincoln Park. Refined and quiet at night.
Lincoln Park
The family favourite: the free zoo, the conservatory, North Avenue Beach, and residential two-flats and condos on leafy streets.
Wrigleyville & Lakeview
Wrigley Field, sports bars, and small theatres. Lively on game nights, well connected by the Red Line.
West Loop
Restaurant Row on Randolph Street, converted lofts, and the city's most sought-after dinner reservations.
Old Town & Wicker Park
Second City comedy in Old Town; independent shops, music venues, and vintage apartments in Wicker Park and Bucktown.
Learn Chicago before you book
Neighborhoods, seasons, and booking tips — the full destination guide.
Read the Chicago guide