Weekend trips from Chicago
15 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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Fort Lauderdale $140
Thu Oct 29 – Mon Nov 2 · 4 nights
Allegiant Air · Nonstop · 3h 10m out · 6 weekends found
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Las Vegas $146
Thu Oct 29 – Mon Nov 2 · 4 nights
Frontier Airlines · 1 stop · 4h 55m out · 7 weekends found
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Atlanta $149
Thu Oct 22 – Mon Oct 26 · 4 nights
Frontier Airlines · Nonstop · 2h 23m out · 4 weekends found
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Denver $155
Fri Nov 6 – Sun Nov 8 · 2 nights
Frontier Airlines · Nonstop · 2h 56m out · 4 weekends found
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Miami $172
Thu Oct 29 – Sun Nov 1 · 3 nights
Frontier Airlines · 1 stop · 3h 10m out · 6 weekends found
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Dallas $180
Sat Oct 31 – Mon Nov 2 · 2 nights
Frontier Airlines · Nonstop · 2h 42m out · 6 weekends found
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Los Angeles $190
Fri Nov 13 – Mon Nov 16 · 3 nights
Southwest Airlines · Nonstop · 4h 30m out · 4 weekends found
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Phoenix $194
Fri Oct 16 – Mon Oct 19 · 3 nights
American Airlines · Nonstop · 3h 59m out · 3 weekends found
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San Juan $203
Fri Oct 23 – Mon Oct 26 · 3 nights
Frontier Airlines · 1 stop · 6h 18m out · 3 weekends found
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Orlando $206
Fri Nov 13 – Mon Nov 16 · 3 nights
Allegiant Air · 1 stop · 2h 36m out · 4 weekends found
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Houston $249
Thu Oct 22 – Sun Oct 25 · 3 nights
Frontier Airlines · 1 stop · 2h 59m out · 2 weekends found
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Boston $250
Fri Nov 20 – Mon Nov 23 · 3 nights
Frontier Airlines · 1 stop · 5h 53m out · 2 weekends found
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Mexico City $251
Thu Nov 12 – Mon Nov 16 · 4 nights
Frontier Airlines · 1 stop · 6h 28m out · 2 weekends found
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New York $267
Fri Dec 11 – Sun Dec 13 · 2 nights
Frontier Airlines · 1 stop · 5h 36m out · 7 weekends found
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San Francisco $309
Fri Oct 23 – Sun Oct 25 · 2 nights
Frontier Airlines · 1 stop · 6h 25m out · 4 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.