Cheap flights from Connecticut to Chicago
Travel > North America > United States > Connecticut to Chicago flights
If you want to visit a vibrant, energetic city that's rich in heritage, culture, entertainment, and commerce, Chicago runs right up there with the big dogs. You could start by visiting downtown which is the center for government, finance, and commerce of Chicago and is encircled by The Loop, named for the elevated train tracks that loop around the central area. Tall skyscrapers such as the world's second-tallest building, the Sears Tower, and the Chicago Board of Trade are landmarks... (read more in our Chicago Travel Guide)
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Cheapest flights found for the next 6 months
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Check our newest flight offers to Chicago:
- $158
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Windsor Locks, CT (BDL) Chicago, IL (ORD) 01/17/2025 01:17 pm Chicago, IL (ORD) Windsor Locks, CT (BDL) 01/26/2025 07:00 am - $313 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Windsor Locks, CT (BDL) Chicago, IL (MDW) 12/29/2024 07:12 pm Chicago, IL (MDW) Windsor Locks, CT (BDL) 01/12/2025 08:45 am - $313 Frontier Airlines
cheapoair.com check priceFrom To Departure Time Windsor Locks, CT (BDL) Chicago, IL (ORD) 12/29/2024 07:12 pm Chicago, IL (ORD) Windsor Locks, CT (BDL) 01/12/2025 07:00 am - $377
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Windsor Locks, CT (BDL) Chicago, IL (ORD) 12/29/2024 06:00 am Chicago, IL (ORD) Windsor Locks, CT (BDL) 01/12/2025 08:45 am - $438 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Windsor Locks, CT (BDL) Chicago, IL (MDW) 12/29/2024 07:12 pm Chicago, IL (MDW) Windsor Locks, CT (BDL) 01/12/2025 03:22 pm
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