$44 Find Cheap Flights from Chicago to Connecticut

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Connecticut departing on 2/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Connecticut

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Connecticut, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Connecticut, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Connecticut Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Connecticut that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Connecticut

Thu, Apr 23 - Mon, Apr 27
Frontier Logo
6:31 am - 10:00 am
ORD
-
JFK
2h 29mnonstop
Frontier Logo
11:04 am - 1:00 pm
JFK
-
ORD
2h 56mnonstop
$76Frontier
Wed, Feb 25 - Wed, Mar 4
Spirit Airlines Logo
5:58 pm - 8:59 pm
ORD
-
LGA
2h 01mnonstop
Spirit Airlines Logo
7:40 am - 9:22 am
LGA
-
ORD
2h 42mnonstop
$77Spirit Airlines
Wed, Mar 18 - Tue, Mar 24
Frontier Logo
12:05 pm - 3:29 pm
ORD
-
JFK
2h 24mnonstop
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
$77Frontier
Tue, Mar 3 - Sat, Mar 7
Multiple Airlines Logo
6:02 pm - 1:08 am
ORD
-
EWR
6h 06m
1 stop
Multiple Airlines Logo
11:05 pm - 12:40 am
EWR
-
ORD
2h 35mnonstop
$107Multiple Airlines
Thu, Mar 5 - Sat, Mar 7
Multiple Airlines Logo
6:15 am - 7:00 pm
MDW
-
LGA
11h 45m
1 stop
Multiple Airlines Logo
12:29 pm - 10:24 pm
LGA
-
MDW
10h 55m
1 stop
$141Multiple Airlines
Tue, Mar 10 - Wed, Mar 11
JetBlue Logo
10:00 am - 11:32 pm
ORD
-
PVD
12h 32m
2 stops
JetBlue Logo
6:30 am - 11:54 am
PVD
-
ORD
6h 24m
1 stop
$215JetBlue
Tue, Mar 10 - Tue, Mar 17
JetBlue Logo
10:00 am - 11:32 pm
ORD
-
PVD
12h 32m
2 stops
JetBlue Logo
6:00 am - 11:25 am
PVD
-
ORD
6h 25m
1 stop
$222JetBlue
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
12:45 pm - 3:50 pm
MDW
-
PVD
2h 05mnonstop
Southwest Logo
3:50 pm - 10:50 pm
PVD
-
MDW
8h 00m
1 stop
$307Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
6:00 pm - 9:10 pm
MDW
-
PVD
2h 10mnonstop
Southwest Logo
12:35 pm - 2:15 pm
PVD
-
MDW
2h 40mnonstop
$309Southwest
Wed, Apr 1 - Wed, Apr 8
Delta Logo
9:35 am - 3:59 pm
MDW
-
PVD
5h 24m
1 stop
Delta Logo
5:29 am - 8:53 am
PVD
-
MDW
4h 24m
1 stop
$317Delta
Booking Insights

KAYAK's insights & trends for Chicago to Connecticut flights

Get data-powered insights and trends into flights from Chicago to Connecticut to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Connecticut?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Connecticut departing in February.

What is the cheapest Chicago to Connecticut flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Connecticut from Chicago found in the last 72 hours was to New Haven, at $77 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Hartford (BDL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $215.

Can I save money by flying with a layover from Chicago to Connecticut?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $266, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Connecticut?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Connecticut, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Connecticut is August, when tickets cost $249 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $413 and $406 respectively.

Good to know

Low seasonFebruary
Cheapest flight$44
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago O'Hare Airport to New York John F Kennedy Airport

FAQs - booking Connecticut flights

  • Where are the most common layovers between Chicago and Connecticut?

    If your flight has one or more stops, you might need to endure layovers at Philadelphia International Airport (PHL), Dulles International Airport (IAD) or Ronald Reagan Washington National Airport (DCA).

  • Which airlines are the best choices for those with kids?

    Many airlines, like American Airlines, will allow parents with young children to board early so they're able to enjoy successful flights. Some, like Delta, will also provide kids with activity kits to help keep them busy on flights.

  • Will I be able to take a pet with me on a flight from Chicago to Connecticut?

    Yes, you will be able to fly with a pet as your carry-on when you're flying to Connecticut through most airlines, but you will need to meet certain requirements. If you're flying with Delta, for instance, your pet will need to be at least 8 weeks old and in good health. It will need to be vaccinated for rabies and fit into a kennel that is no larger than 18 x 11 x 11 inches.

  • What steps can I take to make a flight from Chicago to Connecticut sustainable?

    If you're worried about the sustainability of a flight from Chicago to Connecticut, fly with an airline like American Airlines. They've updated their fleet with fuel-friendly flights and invested in electric equipment to reduce their carbon emissions, with a goal of becoming carbon-neutral by 2050.

  • How does KAYAK find such low prices on flights from Chicago to Connecticut?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Connecticut.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Connecticut?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Connecticut is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Connecticut?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Connecticut with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Connecticut?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Connecticut

  • There are two major airports in Chicago that can get you to Connecticut. Chicago O'Hare International Airport (ORD) is located on the Northwest side of the city, while Chicago Midway International Airport (MDW) is on the Southwest side. Regardless of which Chicago airport you choose, you'll be able to use airlines like American Airlines, Delta, Frontier, Spirit Airlines, and United Airlines to get to Bradley International Airport (BDL) in Connecticut.
  • When flying from Chicago to Connecticut, you might have to make at least one stop. But before you book a flight that includes a layover, search for non-stop flights through airlines like American Airlines and United Airlines. They'll be able to help you get to Connecticut within just 2 to 2.5 hours in many cases.
  • Whether you take a direct flight from Chicago to Connecticut or book one with stops along the way, it would be worth looking into reserving a first-class seat. Some airlines, like Frontier and Spirit Airlines, won't be able to set you up with a first-class experience. But others, like American Airlines, Delta, and United Airlines, can help you get access to a comfortable seat with extra legroom and other amenities in first class.
  • If you're interested in trying to save money while flying from Chicago to Connecticut, you might want to think about packing light for it. If you're able to bring just a carry-on bag that meets your airline's requirements, you can take it on a flight for free. Otherwise, most airlines, including Delta, Frontier, and Spirit Airlines, will charge you extra baggage fees for every bag you check.
  • If you get to Chicago O'Hare International Airport early for a flight to Connecticut and have time to kill, consider visiting a lounge offered by your airline, such as American Airlines' Admirals Club or United Airlines' United Club. Chicago Midway International Airport also has a lounge called Club MDW, which is open to all passengers for a fee.

Reviews of the top 4 airlines serving from Chicago to Connecticut

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Connecticut. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Connecticut? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4283 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

2.0 MediocreMike, Feb 2026
LAS - OKC
Read more Southwest reviews

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

Flight was smooth. We boarded early and left Grand Rapids about a half hour ahead of schedule. We then arrived in Lakeland about 40 minutes early. Flights attendants (3) were welcoming and pleasant. Wish we would have at least been offered to buy a bottle of water. No beverage service at all.

I really liked the young man who checked me in and took my bags! He was so kind and was very helpful! I told my sister about the great service and him and she said that is why she flies Avelo Air.

The flight was delayed by a lot and the seats are pretty tight

Surprisingly was one of the better flights I’ve been on

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

Avelo provided exactly what I expected. They are a low-cost option with no frills but the experience was comfortable and the staff was great! I will be using them in the future for trips when cost is a priority for me.

Expect nothing and you will be fine. Seats are crammed.

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

Everything you need to know for your flight from Chicago to Connecticut

Cabin class types available on flights to Connecticut

Cabin classes available on flights to Connecticut. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.