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$53+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Connecticut (USCT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

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 November 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Tue 12/38:29 pmLGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 12/114:19 pmORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 11/20$113
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Wed 12/45:59 pmLGA - ORD
1 stop15h 25mFrontier
Tue 1/73:00 pmORD - LGA
1 stop6h 00mFrontier
Deal found 11/20$114
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/511:19 amJFK - MDW
1 stop25h 22mFrontier
Mon 12/95:01 amMDW - JFK
1 stop28h 15mFrontier
Deal found 11/20$115
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/106:59 pmEWR - ORD
2 stops16h 33mSpirit Airlines
Tue 12/176:37 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 11/20$120
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/55:59 pmLGA - ORD
1 stop16h 55mMultiple Airlines
Sun 12/810:43 amORD - LGA
Nonstop2h 17mMultiple Airlines
Deal found 11/20$121
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/510:55 pmEWR - ORD
Nonstop2h 39mMultiple Airlines
Mon 12/93:25 pmORD - EWR
1 stop20h 35mMultiple Airlines
Deal found 11/19$124
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Wed 12/43:00 pmJFK - ORD
1 stop18h 24mFrontier
Mon 1/64:02 pmORD - JFK
1 stop17h 01mFrontier
Deal found 11/20$138
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Thu 12/1210:59 pmLGA - MDW
1 stop26h 14mFrontier
Mon 12/169:57 pmMDW - LGA
1 stop17h 32mFrontier
Deal found 11/20$138
This JetBlue deal was found by Cheapflights users on 11/20. 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.
Wed 12/47:29 amJFK - ORD
Nonstop2h 55mJetBlue
Tue 12/1010:14 amORD - JFK
Nonstop2h 16mJetBlue
Deal found 11/20$147
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/139:15 pmLGA - ORD
Nonstop2h 38mUnited Airlines
Wed 12/183:00 pmORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 11/20$147
This Southwest deal was found by Cheapflights users on 11/20. 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.
Fri 12/139:50 pmLGA - MDW
Nonstop2h 25mSouthwest
Wed 12/186:00 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 11/20$148
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/178:05 amJFK - ORD
Nonstop3h 00mDelta
Sat 1/112:00 pmORD - JFK
Nonstop2h 27mDelta
Deal found 11/19$152

Find flights from Connecticut to Chicago within your budget

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 12/3

8:29 pm-10:06 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 12/11

4:19 pm-7:24 pm

Nonstop2h 05m

$113

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 1/18

3:00 pm-9:52 am

1 stop19h 52m

Chicago O'Hare Intl

Mon 1/20

3:16 pm-10:05 am

1 stop17h 49m

$114

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 1/18

11:04 am-3:21 pm

1 stop29h 17m

Chicago Midway

Mon 1/20

7:15 am-10:05 am

1 stop25h 50m

$114

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 1/8

5:00 pm-9:29 am

1 stop17h 29m

Chicago O'Hare Intl

Mon 1/13

5:43 pm-3:56 pm

1 stop21h 13m

$114

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 1/6

5:35 pm-7:19 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 1/11

5:05 am-9:03 am

Nonstop2h 58m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 1/12

10:00 pm-7:40 am

1 stop10h 40m

Chicago O'Hare Intl

Wed 1/15

12:42 pm-9:10 pm

1 stop7h 28m

$118

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 12/5

5:59 pm-9:54 am

1 stop16h 55m

Chicago O'Hare Intl

Sun 12/8

10:43 am-2:00 pm

Nonstop2h 17m

$121

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 12/5

10:55 pm-12:34 am

Nonstop2h 39m

Chicago O'Hare Intl

Mon 12/9

3:25 pm-1:00 pm

1 stop20h 35m

$124

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/22

5:59 pm-3:13 pm

1 stop22h 14m

Chicago Midway

Mon 1/27

6:15 am-3:10 pm

1 stop7h 55m

$124

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 12/4

7:29 am-9:24 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 12/10

10:14 am-1:30 pm

Nonstop2h 16m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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.

Travel insights for flights from Connecticut to Chicago

Get recent, data-driven insights about flights from Connecticut to Chicago including ideal travel times, pricing trends, and more.

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 $232). Flying from Connecticut to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

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 November 21, 2024.

The most flights from USCT to CHI are scheduled on a Monday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 November 21, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, Frontier and JetBlue from Connecticut to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
286 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $53. Users have also found prices from $59 and $74 on Frontier and JetBlue, 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 New York LaGuardia - Chicago O'Hare Intl or Newark - 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: SkyWest Airlines (100%), Republic Airways (100%), ANA( 95%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $970 for a flight from Connecticut to Chicago. The cheapest flight overall is $161 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $133.

  • 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 $232). Flying from Connecticut to Chicago in June is currently the most expensive (average of $308). 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.

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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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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$99Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$117Average$225FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$296FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$190Average$347FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$192Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$399FlexibilityNo cancel feeOn-time69%
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