Cheap flights to
Connecticut

There’s no exact science for finding the best day of the week or exact date ahead of a flight to book for the cheapest flight, but there is a time period when prices tend to be lowest. We call it the Goldilocks Window—not too early, not too late. It’s about 1–3 months before a domestic trip and 2–8 months before an international trip.

If you plan to travel during peak travel season, however, or if you’re traveling for an event and your dates are not flexible, it’s best to look on the earlier side. For trips during December holiday season, you’d be wise to start looking at fares in July, and vice versa for a summer vacation. While it can be tempting to hold out for last-minute deals, they rarely exist. In fact, we’ve found that prices are almost guaranteed to rise at the 21-, 14-, and 7-day points before a trip, so start your search much earlier than that.

Our Greek islands Trick was named for the popular and expensive-to-reach islands, but it can work for numerous destinations, including those with small airports like Connecticut. If you want to fly from Baton Rouge to New Haven in October to see the fall leaves, for example, you could be looking at flights upwards of $350. Instead, look at flights to New York, often found for under $200. From there, you could rent a car or take a train for the last leg.

The idea is just to get the cheapest flight you can that gets you close to where you really want to go, then book a separate cheap flight, car, bus, train, or other mode of transportation to close the gap. Yes, it takes more effort, but it could save you money that you can put toward an extra night or two in a hotel.

If you’re only looking for flights from your home airport, you’re likely missing out on some great deals. This works like the Greek Islands Trick but in reverse. If you want to fly from Madison to New Haven but flights are out of your price range, look for flights from Chicago instead. You could find a cheaper, more direct option that makes taking the bus or driving to O’Hare worth it.

We see deals from airports all over the country every day, and many of them are worth adding an extra leg to your trip. If another airport is within driving distance or easy to reach on public transport, those options can be no-brainers. Sometimes for very expensive flights or flights across the country, it can be worth looking at airports even farther away from home and trying to find a budget flight to a hub airport before you book a flight to your final destination.

Summer and early fall are the busiest times to travel to Connecticut—and therefore the most expensive. The cheapest time to travel is in the winter. However, if you want to save money while also avoiding cold and gray weather, try traveling during shoulder season. The periods just before and after a destination’s high seasons––like April–May and November in Connecticut—are great times to travel for flight and hotel deals, fewer crowds, and generally still some nice weather.

If you can be flexible with your travel dates, you can likely save money any time of year. Play around with flying on alternative dates, and see if there’s a difference between specific weeks. Even in peak seasons, it’s usually cheaper to fly on Tuesdays, Wednesdays, and Saturdays. If you can avoid Fridays and Sundays, when people take weekend trips or travel for business, you’ll likely find lower-priced flights.

Perhaps the easiest way to save money on flights is to let technology take the wheel. Set up fare alerts for your travel dates, and you can stop manually searching and worrying about missing a price drop. It’s best to do this at least a few months before your departure date, as well as to set alerts for multiple dates and airports if you’re flexible.

Connecticut is a small state with small airports. If you’re coming from the East Coast or parts of the Midwest you can likely reach the state on a nonstop flight, but from the rest of the country you’ll probably make one stop. If you’re visiting from outside of the US, you’ll make one or two stops and likely transit through New York.