HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$52+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$105
(Booking.com)

One-way from

$52
(FlightHub)

Good round-trip deal

$365 or less

Good one-way deal

$165 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Springfield (SFY)-Chicago (CHI) flights.
Search Deals
From Connecticut to Chicago (CHI)
Search Deals
One-way flight from Connecticut to Chicago (CHI)
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

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 April 2, 2025.

This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:55 amEWR - ORD
Nonstop2h 32mSpirit Airlines
Tue 5/135:05 amORD - EWR
1 stop10h 29mSpirit Airlines
Deal found 4/1$105
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Thu 5/14:38 pmLGA - ORD
Nonstop2h 39mSpirit Airlines
Mon 5/55:55 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 4/1$122
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/258:00 amJFK - ORD
Nonstop2h 51mDelta
Wed 5/286:18 pmORD - JFK
Nonstop2h 42mDelta
Deal found 4/1$137
This Southwest deal was found by Cheapflights users on 3/31. 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.
Sun 4/206:10 amLGA - MDW
Nonstop2h 20mSouthwest
Thu 4/247:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 3/31$143
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/195:15 pmLGA - ORD
Nonstop2h 37mMultiple Airlines
Thu 4/243:17 pmORD - LGA
1 stop6h 52mMultiple Airlines
Deal found 4/1$148
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:25 pmLGA - ORD
Nonstop2h 55mDelta
Wed 5/286:55 pmORD - LGA
Nonstop2h 22mDelta
Deal found 4/1$153
This JetBlue deal was found by Cheapflights users on 4/1. 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.
Sat 5/248:00 pmJFK - ORD
Nonstop2h 54mJetBlue
Wed 5/286:15 amORD - JFK
Nonstop2h 15mJetBlue
Deal found 4/1$157
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/265:55 amLGA - ORD
Nonstop2h 33mAmerican Airlines
Thu 5/296:37 pmORD - LGA
Nonstop2h 18mAmerican Airlines
Deal found 4/1$159
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/208:59 amJFK - ORD
Nonstop3h 06mAmerican Airlines
Fri 4/255:10 pmORD - JFK
Nonstop2h 20mAmerican Airlines
Deal found 4/1$163
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/299:50 pmEWR - ORD
Nonstop2h 50mUnited Airlines
Tue 5/611:55 amORD - EWR
Nonstop2h 17mUnited Airlines
Deal found 4/1$177
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:30 amEWR - ORD
Nonstop2h 33mMultiple Airlines
Sun 5/48:05 pmORD - EWR
1 stop13h 39mMultiple Airlines
Deal found 4/1$185
This Flightnetwork deal was found by Cheapflights users on 3/31. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:00 amJFK - MDW
1 stop6h 26mFrontier
Wed 5/212:12 pmMDW - JFK
1 stop9h 08mFrontier
Deal found 3/31$194

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 April 2, 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

Thu 5/8

5:55 am-7:27 am

Nonstop2h 32m

Chicago O'Hare Intl

Tue 5/13

5:05 am-4:34 pm

1 stop10h 29m

$105

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/1

4:38 pm-6:17 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 5/5

5:55 am-9:00 am

Nonstop2h 05m

$122

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 5/25

8:00 am-9:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Wed 5/28

6:18 pm-10:00 pm

Nonstop2h 42m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 4/20

6:10 am-7:30 am

Nonstop2h 20m

Chicago Midway

Thu 4/24

7:50 pm-11:00 pm

Nonstop2h 10m

$143

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 4/19

5:15 pm-6:52 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 4/23

9:28 am-4:29 pm

1 stop6h 01m

$148

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 5/21

5:25 pm-7:20 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 5/28

6:55 pm-10:17 pm

Nonstop2h 22m

$153

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 5/24

8:00 pm-9:54 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 5/28

6:15 am-9:30 am

Nonstop2h 15m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 5/26

5:55 am-7:28 am

Nonstop2h 33m

Chicago O'Hare Intl

Fri 5/30

5:12 pm-8:19 pm

Nonstop2h 07m

$159

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 4/20

8:59 am-11:05 am

Nonstop3h 06m

Chicago O'Hare Intl

Fri 4/25

5:10 pm-8:30 pm

Nonstop2h 20m

$163

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 4/29

9:50 pm-11:40 pm

Nonstop2h 50m

Chicago O'Hare Intl

Tue 5/6

11:55 am-3:12 pm

Nonstop2h 17m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 60 results
1
2
3
...
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

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 April 2, 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.

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 April 2, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,823 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,616 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Food

7.1

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $52. Users have also found prices from $69 and $69 on Delta and Southwest, 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 New York John F Kennedy Intl - 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 (95%), ANA (93%), Republic Airways( 91%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $909 for a flight from Connecticut to Chicago. The cheapest flight overall is $114 while the most popular route, (New York LaGuardia - Chicago O'Hare Intl) is currently priced at $68.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Denver to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Diego to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Newark to St. Louis flights
Minneapolis to Midway flights
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Reagan-National to Midway flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
Hartford to O'Hare Intl flights
Seattle to Midway flights
Boston to St. Louis flights
Burbank to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
LaGuardia to St. Louis flights
Cleveland to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Baltimore to Midway flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$202FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$205FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$116Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$125Average$433FlexibilityNo cancel feeOn-time69%
DeltaCheapest$175Average$339FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$205Average$345FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$389FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.