Cheap flights from Connecticut to Chicago from $69
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Connecticut to Chicago departing on 10/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Connecticut to Chicago Midway Airport
Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets
Delta flights from Connecticut to Chicago Midway Airport
Our best Delta deals on Connecticut to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Connecticut to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest Connecticut to Chicago Midway flight route?
Fly from Hartford Bradley Intl to Chicago Midway for the best Connecticut - Chicago Midway flight prices
What cabin class options are available on Connecticut to Chicago Midway flights?
There are 1 cabin classes available to choose from on Connecticut to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Connecticut to Chicago Midway?
Southwest, Delta, and Allegiant Air are the most popular carriers operating from Connecticut to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Avelo Airlines are the top three most popular airlines that fly to Chicago Midway Airport from Connecticut according to our data. Southwest is the first choice among our users, with 79% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 5 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Connecticut to Chicago Midway Airport on average per day?
As of June 2025, there are 8 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 7:00AM, with 46% of flights taking off in the afternoon.
How many flights depart from Connecticut to Chicago Midway Airport on average per week?
The number of flights available between Connecticut and Chicago Midway Airport is 58 per week as of June 2025. The most frequent departure day is Mon, with 22% of weekly flights leaving on this day.
Cheap Connecticut to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago Midway Airport
When did momondo last update prices for flights from Connecticut to Chicago Midway Airport?
Prices for flights from Connecticut to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Connecticut to Chicago Midway Airport?
There are 6 operators available for flights from Connecticut to Chicago Midway Airport as of June 2025.
How old do you have to be to fly from Connecticut to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Connecticut to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Connecticut to Chicago Midway Airport is Boeing 737-800, representing 23.03% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 10.62%, Embraer 175 (Enhanced Winglets) at 10.02%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 9.93%.
Best airlines flying from Connecticut to Chicago Midway Airport
Compare and see reviews for airlines that fly from Connecticut to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $77 | Free Cancellation | Rating 7.4 76 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 8.0 7,962 reviews | |||
| PriceFrom $190 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $299 | Free Cancellation | Rating 7.4 8,830 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Connecticut to Chicago?
Finding the right flight to Chicago from Connecticut is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Connecticut to Chicago with flexible booking policies on momondo?
Flights from Connecticut to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Connecticut to Chicago?
Once all potential Connecticut to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Connecticut to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Connecticut and alert you when they change.