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From Chicago

Weekend getaways from Chicago

Chicago's weekend map runs north and around the lake: Wisconsin's resort lakes an hour or two out, Michigan's wine-country lakeshore a bit further, and a short flight to mountain towns when you want a bigger change of scene.

We rank each option by real door-to-door time from the city and plan the whole trip — so a Friday getaway is spent by the water, not on I-94.

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Ranked by real travel time from Chicago

Each getaway below shows its true door-to-door time — the same journey our planner uses, ferries and traffic included — so you can judge the weekend before you commit.

For a bigger change of scene, a short flight opens up Nashville's music and food and the Colorado mountain towns — we show the real flight time and the sensible airport.

Good questions

What's the best weekend getaway from Chicago?

For the shortest escape, Lake Geneva in Wisconsin (about 90 minutes) for a lakeside-resort weekend. For wine country and Lake Michigan beaches, Traverse City. For a bigger change, a short flight to Nashville or the Colorado mountains. We rank by real travel time.

Where can you drive for a weekend from Chicago?

Lake Geneva (Wisconsin) and the wider Wisconsin lakes are the classic short drives; Traverse City in Michigan is a longer but rewarding haul for wine country and beaches. We show the real drive time and plan the trip.

Where's good for a quick flight getaway from Chicago?

Nashville for music, food and a livelier weekend; Aspen and the Colorado mountains for the outdoors and spas. Both are short flights from O'Hare or Midway — we pick the sensible airport and time it.

Weekend getaways by city

Your getaway, assembled

Tell us where you’re starting.

We’ll build the whole trip — travel, a checked stay and the local dinners and walks worth making time for — around your city and your dates.

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