$54 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 5/2. 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 30 - Thu, May 7
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
Spirit Airlines Logo
6:29 pm - 8:11 pm
LGA
-
ORD
2h 42mnonstop
$100Spirit Airlines
Thu, Apr 23 - Sat, Apr 25
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
Spirit Airlines Logo
2:38 pm - 4:14 pm
LGA
-
ORD
2h 36mnonstop
$102Spirit Airlines
Sun, Apr 19 - Tue, Apr 21
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$112Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$113Frontier
Tue, Jun 16 - Sat, Jul 4
American Airlines Logo
10:53 am - 2:30 pm
ORD
-
JFK
2h 37mnonstop
American Airlines Logo
8:00 am - 10:04 am
JFK
-
ORD
3h 04mnonstop
$119American Airlines
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
4:28 pm - 1:16 am
ORD
-
EWR
7h 48m
1 stop
Multiple Airlines Logo
10:08 am - 11:42 am
EWR
-
ORD
2h 34mnonstop
$120Multiple Airlines
Thu, Apr 30 - Mon, May 4
Multiple Airlines Logo
12:47 pm - 3:54 pm
ORD
-
EWR
2h 07mnonstop
Multiple Airlines Logo
10:29 pm - 7:55 am
EWR
-
ORD
10h 26m
1 stop
$125Multiple Airlines
Wed, May 27 - Sat, Jun 13
American Airlines Logo
4:29 pm - 8:04 pm
ORD
-
JFK
2h 35mnonstop
American Airlines Logo
1:50 pm - 3:44 pm
JFK
-
ORD
2h 54mnonstop
$153American Airlines
Wed, Apr 22 - Tue, May 5
Southwest Logo
7:40 am - 10:50 am
MDW
-
PVD
2h 10mnonstop
Southwest Logo
7:45 am - 9:15 am
PVD
-
MDW
2h 30mnonstop
$257Southwest
Wed, May 20 - Tue, May 26
Southwest Logo
7:40 am - 10:50 am
MDW
-
PVD
2h 10mnonstop
Southwest Logo
6:25 am - 10:40 am
PVD
-
MDW
5h 15m
1 stop
$267Southwest
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 April.

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 $75 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 $333.

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 $295, 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 $247 (return) on average. On the other hand, the most expensive months are April and March, when the average cost of round-trip tickets is $489 and $457 respectively.

Good to know

Low seasonFebruary
Cheapest flight$54
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago O'Hare Airport to Newark Liberty 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 4339 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

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.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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.