Cheap flights from Connecticut (CT) to Chicago (CHI)

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How to find the cheapest flight from
Connecticut to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Connecticut to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
When is the cheapest time to fly from Connecticut to Chicago (CT - CHI)?

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.

Cheap flights from Connecticut to Chicago in June, July 2022

The best prices found for Connecticut to CHI flights for June, July
11 Jul - 13 Jul
$184pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
4 Jul - 12 Jul
$189pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
19 Jul - 20 Jul
$196pp
BDL
Hartford Bradley Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
BDL
Hartford Bradley Intl

Connecticut to Chicago 2022 flight deals

Cheap flights to Chicago from Connecticut found for this year
10 Sep - 12 Sep
$178pp
BDL
Hartford Bradley Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
11 Jul - 13 Jul
$184pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
10 Sep - 13 Sep
$185pp
BDL
Hartford Bradley Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl

Non-stop flights to Chicago from Connecticut

Save time with Connecticut to Chicago direct flight deals
10 Sep - 12 Sep
$178pp
BDL
Hartford Bradley Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
24 Sep - 27 Sep
$208pp
BDL
Hartford Bradley Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl
19 Oct - 21 Oct
$236pp
BDL
Hartford Bradley Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BDL
Hartford Bradley Intl

Last minute flights from Connecticut to Chicago

Late deals on round-trip flights to Chicago from Connecticut, departing today and this week
4 Jul - 12 Jul
$189pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
3 Jul - 6 Jul
$217pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl
7 Jul - 13 Jul
$221pp
BDL
Hartford Bradley Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BDL
Hartford Bradley Intl

One-way flights to Chicago from Connecticut

The cheapest one-way flights from Connecticut to Chicago
1:45 am - 5:13 am
Delta
1 Stop
4h 28m
BDL - ORD
Delta
$138
Delta
5:59 pm - 2:38 am
Frontier
1 Stop
9h 39m
BDL - MDW
Frontier
$145
Kiwi.com
2:08 pm - 3:47 pm
United Airlines
Nonstop
2h 39m
BDL - ORD
United Airlines
$149
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Connecticut</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Connecticut to Chicago

Which airlines flying from Connecticut to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, American Airlines, and Spirit Airlines flying from Connecticut to Chicago have implemented new flexible cancellation policies.

Can I find flights from Connecticut to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Connecticut to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $178, but on average you can expect to pay $207.

Are there nonstop flights from Connecticut to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Connecticut to Chicago under $200. A good price for a nonstop flight from Connecticut to Chicago is less than $272.

Are there last-minute flights available from Connecticut to Chicago for under $200?

There are currently 20+ open flights from Connecticut to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Connecticut to Chicago?

You can find nonstop flights on the following days: Monday, Tuesday, Wednesday, Thursday, Saturday.

How many flights depart from Connecticut to Chicago on average per day?

17 flight departures from Connecticut to Chicago per day on average.
Morning (6am - Noon) - 71% of flight departures
Afternoon (Noon - 6pm) - 29% of flight departures

How long is the flight from Connecticut to Chicago?

A quick flight from Connecticut to Chicago can take about 2h 38m. American Airlines provides one of the quickest options available for as low as $178. Airlines will cover a distance of 785 mi. This flight may include one or multiple stops.

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 $80. Users have also found prices from $89 and $98 on United Airlines and Delta, respectively.

What are the most popular routes from Connecticut to Chicago?

The most popular route from Connecticut to Chicago is Hartford Bradley Intl - Chicago O'Hare Intl. You may also consider Hartford Bradley Intl - Chicago Midway or Hartford Bradley Intl - Chicago Greater Rockford.

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 (98%), Air New Zealand( 92%).

What are the most popular airlines that fly from Connecticut to Chicago?

When booking a flight from Connecticut to Chicago, you may want to consider flying on American Airlines, Delta or Juneyao Airlines as they are the most popular for this route.

What are the cheapest flights from Connecticut to Chicago?

On average you can expect to pay $594 for a flight from Connecticut to Chicago. The cheapest flight overall is $89 while the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl) is currently priced at $187.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Connecticut?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Connecticut need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Connecticut are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Connecticut are not required to quarantine after entering Chicago.

Do I need a test to fly back to Connecticut from Chicago?

Returning to Connecticut from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Connecticut.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Connecticut.

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Connecticut to Chicago

Select to see more specific information for flights to Chicago from all departure points in Connecticut.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Connecticut to Chicago.
Flight duration from Connecticut to Chicago
2h 24m
Average temperature for June in Chicago
78.8 °F
Avg rainfall for June in Chicago
3.4 ″

Airports servicing

New Haven (HVN)

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Connecticut to Chicago

The chart below displays the airlines Cheapflights users traveling from Connecticut to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$16 $22 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Spirit Airlines
$74 $188 No cancel fee 65%
American Airlines
$140 $368 No cancel fee 71%
Avelo Airlines
$156 $223 No cancel fee N/A

We couldn't confirm the COVID-19 safety measures taken by Avelo Airlines. Please check directly on their website for additional information.

United Airlines
$159 $323 No cancel fee 69%
Delta
$180 $376 No cancel fee N/A
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