Departing from Chicago
Best Deals from Chicago
We scan 50+ destinations from Midway Intl (MDW) every 6 hours and surface the best all-in trips — flights, hotel, food, and activities.
First scan pending — check back in a few hours or search manually below
Search by vibe
Deal scanner is warming up. Search manually while you wait.
Search by total budget
All-in price per trip, including flights from Chicago.
Popular destinations from Chicago
Click any destination to see budget details, best time to visit, and what it costs.
Cancún
Mexico
Caribbean CoastPrice from MDW →
Montego Bay
Jamaica
CaribbeanPrice from MDW →
Nassau
Bahamas
CaribbeanPrice from MDW →
Hamilton
Bermuda
AtlanticPrice from MDW →
San Juan
Puerto Rico
CaribbeanPrice from MDW →
Punta Cana
Dominican Republic
CaribbeanPrice from MDW →
Liberia
Costa Rica
GuanacastePrice from MDW →
San José
Costa Rica
Central ValleyPrice from MDW →
Grand Cayman
Cayman Islands
CaribbeanPrice from MDW →
Oranjestad
Aruba
CaribbeanPrice from MDW →
St. Maarten
Sint Maarten
CaribbeanPrice from MDW →
New York
USA
NortheastPrice from MDW →