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$39 Find cheap flights from Connecticut to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/28. 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
0 bags
Sat 6/29
Sat 7/6

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In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

May

Cheapest flight

$39
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Newark Liberty Airport to Chicago O'Hare Airport

FAQs for booking flights from Connecticut to Chicago

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

    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 Connecticut to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Connecticut to Chicago?

    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 to Chicago with an airline and back to Connecticut with another airline.

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

    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 to Chicago from Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Connecticut to Chicago?

Find which airlines fly direct from Connecticut to Chicago, which days they fly and book direct flights.

Nonstop departures

Connecticut to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights

Nonstop returns

Chicago to Connecticut

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights
See more direct flights

Book cheap flights from Connecticut to Chicago

Recent round-trip flight deals

8/20Tue
nonstopSpirit Airlines
2h 39mLGA-ORD
8/24Sat
nonstopSpirit Airlines
2h 12mORD-LGA
$59
9/14Sat
nonstopSpirit Airlines
2h 37mLGA-ORD
9/21Sat
nonstopSpirit Airlines
2h 11mORD-LGA
$60
6/11Tue
nonstop
2h 42mLGA-ORD
6/15Sat
1 stop
8h 08mORD-LGA
$76
6/10Mon
1 stop
6h 52mLGA-ORD
6/15Sat
nonstop
2h 18mORD-LGA
$91
9/10Tue
1 stopFrontier
10h 53mLGA-MDW
9/14Sat
1 stopFrontier
15h 00mMDW-LGA
$115
8/31Sat
1 stopFrontier
14h 02mLGA-MDW
9/3Tue
1 stopFrontier
11h 22mMDW-LGA
$116
8/24Sat
nonstopJetBlue
2h 45mJFK-ORD
8/27Tue
nonstopJetBlue
2h 25mORD-JFK
$127
9/3Tue
nonstopDelta
2h 54mLGA-ORD
9/7Sat
nonstopDelta
2h 23mORD-LGA
$139
8/13Tue
nonstopJetBlue
2h 45mJFK-ORD
8/15Thu
nonstopJetBlue
2h 25mORD-JFK
$148
9/4Wed
nonstopDelta
2h 34mLGA-ORD
9/12Thu
nonstopDelta
2h 17mORD-LGA
$154

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/28Wed
1 stopSpirit Airlines
6h 34mEWR-ORD
$39
7/10Wed
nonstopSpirit Airlines
2h 40mEWR-ORD
$40
6/11Tue
1 stopFrontier
6h 12mBDL-ORD
$58
8/20Tue
1 stopFrontier
5h 50mLGA-MDW
$58
8/19Mon
nonstopAmerican Airlines
2h 37mEWR-ORD
$60
6/25Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
$64
6/25Tue
nonstopJetBlue
2h 43mJFK-ORD
$64
8/21Wed
1 stopDelta
4h 04mEWR-MDW
$78
8/31Sat
1 stopDelta
7h 33mEWR-ORD
$78
6/5Wed
nonstopJetBlue
2h 50mJFK-ORD
$91

Search by stops

Search by airline

Search by price

Last minute flights from Connecticut to Chicago

Last minute flight, train and bus deals

6/4Tue
nonstopSpirit Airlines
2h 39mLGA-ORD
6/11Tue
multi-stopSpirit Airlines
15h 24mORD-LGA
$81
6/4Tue
multi-stopSpirit Airlines
11h 29mLGA-ORD
6/11Tue
multi-stopSpirit Airlines
21h 10mORD-LGA
$89
6/3Mon
multi-stopFrontier
6h 40mLGA-ORD
6/10Mon
multi-stopFrontier
23h 17mORD-LGA
$165
6/3Mon
multi-stopFrontier
6h 40mLGA-ORD
6/14Fri
multi-stopFrontier
26h 36mORD-LGA
$196
6/3Mon
multi-stop
7h 16mLGA-ORD
6/4Tue
multi-stop
13h 20mORD-LGA
$197
6/4Tue
multi-stop
18h 51mBDL-ORD
6/5Wed
multi-stop
26h 59mORD-BDL
$227
6/4Tue
nonstopAmerican Airlines
2h 40mEWR-ORD
6/9Sun
nonstopAmerican Airlines
2h 04mORD-EWR
$242
6/1Sat
nonstopJetBlue
2h 50mJFK-ORD
8/28Wed
nonstopJetBlue
2h 19mORD-JFK
$277
6/1Sat
nonstopAmerican Airlines
2h 40mEWR-ORD
7/1Mon
nonstopAmerican Airlines
2h 04mORD-EWR
$298
6/1Sat
nonstopJetBlue
2h 50mJFK-ORD
7/12Fri
nonstopJetBlue
2h 20mORD-JFK
$298

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Connecticut

Cabin classes:

$732
$751
$531
$132