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$73+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Cheap 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 May 5, 2026.

This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/284:59 pm
LGA
-
ORD
1 stop7h 16m
Spirit Airlines
Wed 6/31:49 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/30$152
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:47 pm
LGA
-
ORD
Nonstop2h 38m
Spirit Airlines
Tue 6/1610:54 am
ORD
-
LGA
1 stop10h 11m
Spirit Airlines
Deal found 5/1$154
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:47 pm
LGA
-
ORD
Nonstop2h 38m
Multiple Airlines
Fri 6/51:29 pm
ORD
-
LGA
1 stop6h 27m
Multiple Airlines
Deal found 4/30$155
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:59 am
LGA
-
ORD
1 stop13h 16m
Spirit Airlines
Fri 5/291:49 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/30$156
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:47 pm
LGA
-
ORD
Nonstop2h 38m
Spirit Airlines
Fri 6/51:49 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/30$157
This Expedia deal was found by Cheapflights users on 5/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:00 pm
JFK
-
ORD
1 stop7h 41m
Multiple Airlines
Sat 6/136:00 am
ORD
-
JFK
Nonstop2h 20m
Multiple Airlines
Deal found 5/3$159
This Expedia deal was found by Cheapflights users on 5/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 pm
LGA
-
ORD
1 stop10h 55m
Frontier
Tue 6/26:55 am
ORD
-
LGA
1 stop9h 53m
Frontier
Deal found 5/4$160
This flygcity.se deal was found by Cheapflights users on 5/3. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 am
JFK
-
ORD
Nonstop2h 45m
JetBlue
Fri 6/196:00 am
ORD
-
JFK
Nonstop2h 20m
JetBlue
Deal found 5/3$161
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 pm
LGA
-
ORD
1 stop10h 55m
Frontier
Fri 5/291:50 pm
ORD
-
LGA
1 stop8h 24m
Frontier
Deal found 5/1$161
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Thu 6/41:00 pm
JFK
-
MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
-
JFK
1 stop22h 55m
Frontier
Deal found 5/4$162
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Thu 6/46:29 am
LGA
-
MDW
1 stop16h 33m
Frontier
Mon 6/812:04 pm
MDW
-
LGA
1 stop28h 49m
Frontier
Deal found 5/4$162
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:01 pm
EWR
-
ORD
Nonstop2h 37m
Spirit Airlines
Thu 6/412:54 pm
ORD
-
EWR
Nonstop2h 05m
Spirit Airlines
Deal found 4/30$163

Find flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated May 5, 2026.

Round-trip from

$152
(Expedia)

One-way from

$73
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$410

Good round-trip deal

$142 or less

Good one-way deal

$132 or less
From Connecticut to Chicago (CHI)
Search Deals
One-way flight from Connecticut to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Connecticut to Chicago (CHI).
Search Deals

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 May 5, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 7/25

7:35 pm-9:52 pm

Nonstop3h 17m

Chicago O'Hare Intl

Wed 8/5

6:00 am-9:24 am

Nonstop2h 24m

$177

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 9/1

7:05 am-8:48 am

Nonstop2h 43m

Chicago O'Hare Intl

Wed 9/2

6:00 am-9:17 am

Nonstop2h 17m

$177

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 8/11

7:00 am-8:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Sat 8/15

6:00 am-9:13 am

Nonstop2h 13m

$177

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 6/20

7:12 pm-9:00 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sat 7/25

6:00 am-9:12 am

Nonstop2h 12m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 7/9

6:00 am-7:32 am

Nonstop2h 32m

Chicago O'Hare Intl

Mon 7/13

7:05 pm-10:34 pm

Nonstop2h 29m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 8/11

8:25 pm-10:05 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sat 8/15

8:00 pm-11:22 pm

Nonstop2h 22m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 7/23

7:30 am-9:06 am

Nonstop2h 36m

Chicago O'Hare Intl

Sat 7/25

4:00 pm-7:35 pm

Nonstop2h 35m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/20

7:00 am-8:29 am

Nonstop2h 29m

Chicago O'Hare Intl

Sat 7/25

3:00 pm-6:22 pm

Nonstop2h 22m

$177

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 6/28

7:00 am-8:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Wed 7/8

9:39 am-12:55 pm

Nonstop2h 16m

$192

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 8/17

7:05 am-8:48 am

Nonstop2h 43m

Chicago O'Hare Intl

Tue 8/25

6:00 am-9:17 am

Nonstop2h 17m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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

How far ahead should I book a flight from Connecticut to Chicago?

The best time to book flights from Connecticut to Chicago is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $51). Flying from Connecticut to Chicago in July is currently the most expensive (average of $157). 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 May 5, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 25% on flights from Connecticut to Chicago by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 5, 2026.

The most flights from USCT to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

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

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.

  • How long is the flight from Connecticut to Chicago?

    A quick flight from Connecticut to Chicago can take about 2h 43m. Delta provides one of the quickest options available for as low as $177. Airlines will cover a distance of 738 mi. All flights are typically nonstop.

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

    For one-way options, check prices for Avelo Airlines. According to our data, you can fly for as low as $37. Users have also found prices from $68 and $78 on Southwest and American Airlines, respectively.

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

    The most popular route from Connecticut to Chicago is New York LaGuardia - Chicago O'Hare Intl. You may also consider Newark - Chicago O'Hare Intl or New York John F Kennedy Intl - 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: Copa Airlines (100%), ANA (86%), SkyWest Airlines( 85%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $771 for a flight from Connecticut to Chicago. The cheapest flight overall is $166 while the most popular route, (New York LaGuardia - Chicago O'Hare Intl) is currently priced at $142.

  • 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, September is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $51). Flying from Connecticut to Chicago in July is currently the most expensive (average of $157). 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 Chicago?

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

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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.
LaGuardia to O'Hare Intl flights
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George Bush Intcntl to O'Hare Intl flights
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Atlanta to Midway flights
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San Diego to O'Hare Intl flights
Hobby to Midway flights
Los Angeles to Midway flights
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Newark to St. Louis flights
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Sacramento to O'Hare Intl flights
Philadelphia to Midway flights
Raleigh to Midway flights
Las Vegas to O'Hare Intl flights
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Love Field to O'Hare Intl flights
Minneapolis to Midway flights

Top 5 airlines flying from Connecticut to Chicago

Discover the top 5 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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$188FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$157Average$366FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$244FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$184Average$396FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$406FlexibilityNo cancel feeOn-time69%

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