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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 9/10. 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
dom 6/30
dom 7/7

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In the last 7 days travelers have searched 42,787,818 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

8/28mer
nonstopSpirit Airlines
2h 39mLGA-ORD
9/4mer
nonstopSpirit Airlines
2h 11mORD-LGA
$56
9/25mer
nonstopSpirit Airlines
2h 39mLGA-ORD
9/28sab
nonstopSpirit Airlines
2h 12mORD-LGA
$59
6/11mar
nonstop
2h 42mLGA-ORD
6/15sab
1 stop
8h 08mORD-LGA
$76
9/3mar
1 stop
7h 16mLGA-ORD
9/11mer
nonstop
2h 11mORD-LGA
$84
8/21mer
1 stopFrontier
16h 55mLGA-MDW
8/28mer
1 stopFrontier
10h 03mMDW-LGA
$113
9/25mer
1 stopFrontier
5h 29mLGA-MDW
9/28sab
1 stopFrontier
15h 00mMDW-LGA
$114
8/13mar
nonstopJetBlue
2h 45mJFK-ORD
8/20mar
nonstopJetBlue
2h 25mORD-JFK
$127
8/17sab
nonstopDelta
2h 59mLGA-ORD
8/21mer
nonstopDelta
2h 24mORD-LGA
$127
8/24sab
nonstopDelta
2h 59mLGA-ORD
9/3mar
nonstopDelta
2h 09mORD-LGA
$132
8/13mar
nonstopJetBlue
2h 45mJFK-ORD
8/16ven
nonstopJetBlue
2h 25mORD-JFK
$148

Search by stops

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Recent one-way flight deals

9/10mar
1 stopSpirit Airlines
9h 59mEWR-ORD
$39
6/11mar
1 stopSpirit Airlines
10h 55mEWR-ORD
$40
8/20mar
1 stopFrontier
7h 16mLGA-ORD
$58
6/11mar
1 stopFrontier
6h 12mBDL-ORD
$58
8/19lun
nonstopAmerican Airlines
2h 37mEWR-ORD
$60
6/25mar
nonstopJetBlue
2h 43mJFK-ORD
$64
7/30mar
nonstopDelta
2h 29mLGA-ORD
$64
8/31sab
1 stopDelta
4h 43mEWR-ORD
$78
7/5ven
nonstopAmerican Airlines
2h 35mEWR-ORD
$85
7/5ven
nonstopJetBlue
2h 43mJFK-ORD
$85

Search by stops

Search by airline

Search by price

Last minute flights from Connecticut to Chicago

Last minute flight, train and bus deals

6/4mar
multi-stopFrontier
13h 47mLGA-ORD
6/11mar
multi-stopFrontier
15h 00mORD-LGA
$110
6/5mer
multi-stop
7h 16mLGA-ORD
6/14ven
multi-stop
13h 04mORD-LGA
$125
6/5mer
nonstopSpirit Airlines
2h 38mLGA-ORD
6/10lun
multi-stopSpirit Airlines
10h 04mORD-LGA
$130
6/5mer
multi-stopSpirit Airlines
14h 27mLGA-ORD
6/8sab
nonstopSpirit Airlines
1h 57mORD-LGA
$145
6/5mer
nonstopJetBlue
2h 56mJFK-ORD
6/5mer
nonstopJetBlue
2h 28mORD-JFK
$181
6/5mer
nonstopAmerican Airlines
2h 34mEWR-ORD
6/11mar
nonstopAmerican Airlines
2h 20mORD-EWR
$204
6/5mer
nonstopDelta
2h 35mLGA-ORD
6/10lun
nonstopDelta
2h 09mORD-LGA
$214
6/5mer
nonstopAmerican Airlines
2h 34mLGA-ORD
6/6gio
nonstopAmerican Airlines
2h 04mORD-LGA
$229
6/5mer
nonstopDelta
2h 42mJFK-ORD
6/11mar
nonstopDelta
2h 35mORD-JFK
$289
6/1sab
nonstopJetBlue
2h 50mJFK-ORD
7/12ven
nonstopJetBlue
2h 20mORD-JFK
$298

Search by stops

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Search by price

Flights to Chicago

Return flight deals:

Chicago - Connecticut

Cabin classes:

$732
$751
$531
$132