Weekend trips from Chicago
13 places you can reach for a long weekend: leave Thursday, Friday or Saturday, back Sunday or Monday, 2–4 nights. Cheapest weekend first.
Prices updated · per person, round trip, can change at any time
Weekend round trips from Chicago
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Miami $143
Thu Dec 10 – Mon Dec 14 · 4 nights
Frontier Airlines · 1 stop · 4h 56m out · 5 weekends found
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Fort Lauderdale $180
Fri Dec 18 – Mon Dec 21 · 3 nights
Frontier Airlines · 1 stop · 4h 55m out · 5 weekends found
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Tampa $201
Fri Dec 4 – Mon Dec 7 · 3 nights
Frontier Airlines · 1 stop · 3h 50m out · 2 weekends found
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New York $237
Sat Jan 9 – Mon Jan 11 · 2 nights
Frontier Airlines · 1 stop · 4h 32m out · 5 weekends found
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Los Angeles $248
Fri Dec 11 – Mon Dec 14 · 3 nights
Frontier Airlines · 1 stop · 5h 29m out · 2 weekends found
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Houston $260
Thu Dec 10 – Sun Dec 13 · 3 nights
Frontier Airlines · 1 stop · 3h 09m out · 2 weekends found
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Boston $271
Fri Dec 11 – Sun Dec 13 · 2 nights
Frontier Airlines · 1 stop · 6h 06m out · 3 weekends found
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Las Vegas $279
Thu Nov 26 – Mon Nov 30 · 4 nights
Frontier Airlines · Nonstop · 4h 12m out · 2 weekends found
Weekend trips: 2–4 nights, leaving Thursday, Friday or Saturday and returning Sunday or Monday, outbound flight up to 7 hours when known. Prices change often; the booking site shows the final price.
Watch a weekend trip
Pick a destination, the months you can travel and your max price. We check every date in your window and email you when a round trip from Chicago drops below it.