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$64+ Cheap flights from Connecticut to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated julio 3, 2025.

Round-trip from

$132
(Priceline)

One-way from

$64
(FlightHub)

Good round-trip deal

$51 or less

Good one-way deal

$129 or less
From Connecticut to Chicago (CHI)
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One-way flight from Connecticut to Chicago (CHI)
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Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
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Price to beat on a one-way flight from Connecticut to Chicago (CHI).
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Find flight deals from Connecticut to Chicago

Cheapest flights from Connecticut to Chicago
Explore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/169:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
dom. 10/195:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 7/3$130
This Priceline deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2911:04 amEWR - ORD
1 stop6h 34mMultiple Airlines
lun. 8/44:37 pmORD - EWR
1 stop6h 35mMultiple Airlines
Deal found 7/2$132
This Priceline deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/1412:59 pmJFK - ORD
1 stop8h 10mFrontier
dom. 10/195:10 amORD - JFK
1 stop5h 49mFrontier
Deal found 7/2$136
This JetBlue deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/309:29 amJFK - ORD
Nonstop2h 49mJetBlue
mar. 9/211:35 amORD - JFK
Nonstop2h 23mJetBlue
Deal found 7/1$137
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/153:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
vie. 9/2611:13 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 7/1$137
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/307:30 amLGA - MDW
Nonstop2h 20mSouthwest
mié. 9/35:55 pmMDW - LGA
Nonstop2h 15mSouthwest
Deal found 7/2$137
This Priceline deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/235:55 amEWR - ORD
1 stop6h 41mFrontier
mié. 8/272:40 pmORD - EWR
1 stop8h 33mFrontier
Deal found 7/2$139
This Priceline deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/236:30 amLGA - ORD
1 stop10h 34mMultiple Airlines
mar. 7/298:09 amORD - LGA
1 stop8h 21mMultiple Airlines
Deal found 7/1$139
This Priceline deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1911:15 amEWR - MDW
1 stop5h 43mFrontier
lun. 9/225:04 pmMDW - EWR
1 stop6h 30mFrontier
Deal found 7/3$141
This Priceline deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/96:30 amLGA - MDW
1 stop10h 28mFrontier
sáb. 9/1311:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 6/30$144
This Priceline deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/249:00 amJFK - MDW
1 stop10h 18mFrontier
dom. 10/2610:03 pmMDW - JFK
1 stop11h 22mFrontier
Deal found 7/2$146
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/38:15 pmEWR - ORD
Nonstop2h 41mUnited Airlines
sáb. 9/610:35 amORD - EWR
Nonstop2h 17mUnited Airlines
Deal found 7/2$147

Cheapflights Fare Finder

Customize your flight search to find flights from Connecticut to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 3, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Connecticut

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

jue. 10/16

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

dom. 10/19

5:10 pm-8:28 pm

Nonstop2h 18m

$130

NewarkChicago

EWR - ORD

EWRORD

Newark

mar. 7/29

11:04 am-4:38 pm

1 stop6h 34m

Chicago O'Hare Intl

lun. 8/4

4:37 pm-12:12 am

1 stop6h 35m

$132

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 8/30

9:29 am-11:18 am

Nonstop2h 49m

Chicago O'Hare Intl

mar. 9/2

11:35 am-2:58 pm

Nonstop2h 23m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

sáb. 8/30

7:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

mar. 9/2

6:00 am-9:00 am

Nonstop2h 00m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

lun. 9/15

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

vie. 9/26

11:13 am-2:18 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

jue. 7/31

6:59 am-3:27 pm

1 stop9h 28m

Chicago O'Hare Intl

sáb. 8/2

5:07 pm-12:42 am

1 stop6h 35m

$138

NewarkChicago

EWR - ORD

EWRORD

Newark

sáb. 8/23

5:55 am-11:36 am

1 stop6h 41m

Chicago O'Hare Intl

mié. 8/27

2:40 pm-12:13 am

1 stop8h 33m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 7/23

6:30 am-4:04 pm

1 stop10h 34m

Chicago O'Hare Intl

mar. 7/29

8:09 am-5:30 pm

1 stop8h 21m

$139

NewarkChicago

EWR - MDW

EWRMDW

Newark

vie. 9/19

11:15 am-3:58 pm

1 stop5h 43m

Chicago Midway

lun. 9/22

5:04 pm-12:34 am

1 stop6h 30m

$141

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mar. 9/9

6:30 am-3:58 pm

1 stop10h 28m

Chicago Midway

sáb. 9/13

11:23 am-8:02 pm

1 stop7h 39m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Connecticut to Chicago?

Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $245). Flying from Connecticut to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CT to CHI?

Find hourly flight availability from Connecticut to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 3, 2025.

When flying from Connecticut to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Connecticut to Chicago

Explore weekly flight availability from Connecticut to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julio 3, 2025.

The most flights from USCT to CHI are scheduled on a Thursday (23 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Connecticut to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated julio 3, 2025.
Read through reviews of airlines operating flights from Connecticut to Chicago, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,916 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Connecticut to Chicago one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $64. Users have also found prices from $66 and $74 on Frontier and United Airlines, respectively.

  • What are the most popular routes from Connecticut to Chicago?

    The most popular route from Connecticut to Chicago is New York John F Kennedy Intl - Chicago O'Hare Intl. You may also consider Newark - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl.

  • What are the most reliable airlines from Connecticut to Chicago?

    Before booking your flight to Chicago from Connecticut, check out the most reliable airlines to get you to your destination on time: Republic Airways (100%), ANA (89%), Envoy Air( 77%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $1,223 for a flight from Connecticut to Chicago. The cheapest flight overall is $114 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $137.

  • Can I find deals for flights from Connecticut to Chicago that include hotel bookings?

    Yes. In addition to deals on Connecticut to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Chicago.

  • Can I find deals for business class flights from Connecticut to Chicago?

    Yes. Cheapflights offers flight deals from Connecticut to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $245). Flying from Connecticut to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Connecticut?

Book flights to Connecticut if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Connecticut to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
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Hobby to Midway flights
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Tampa to Midway flights
Oakland to O'Hare Intl flights
Newark to St. Louis flights
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Sacramento to O'Hare Intl flights
Love Field to O'Hare Intl flights
LaGuardia to St. Louis flights

Top 7 airlines flying from Connecticut to Chicago

Discover the top 7 airlines that operate flights from Connecticut to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$176FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$222FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$263FlexibilityNo cancel feeOn-time65%
DeltaCheapest$176Average$301FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$199Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$438FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$372FlexibilityNo cancel feeOn-time63%

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