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 2021: compare Connecticut to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
How far in advance should I book a flight from Connecticut to Chicago?

Users have found that booking a flight from Connecticut to Chicago at least 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Connecticut to Chicago for as little as $137 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $157 for flights departing within the next 3 days.

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

April can be a great time to fly to Chicago from Connecticut with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

Cheap flights from Connecticut to Chicago in May, June 2021

The best prices found for Connecticut to CHI flights for May, June
15 Jun - 22 Jun
$185pp
BDL
Hartford Bradley Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BDL
Hartford Bradley Intl
4 Jun - 7 Jun
$202pp
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
2 Jun - 9 Jun
$214pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BDL
Hartford Bradley Intl

Connecticut to Chicago 2021 flight deals

Cheap flights to Chicago from Connecticut found for this year
15 Jun - 22 Jun
$185pp
BDL
Hartford Bradley Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BDL
Hartford Bradley Intl
4 Jun - 7 Jun
$202pp
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
2 Jun - 9 Jun
$214pp
BDL
Hartford Bradley Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BDL
Hartford Bradley Intl

Non-stop flights to Chicago from Connecticut

Save time with Connecticut to Chicago direct flight deals
23 Sep - 27 Sep
$219pp
BDL
Hartford Bradley Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BDL
Hartford Bradley Intl
16 Sep - 19 Sep
$239pp
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
10 Sep - 12 Sep
$259pp
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
20 May - 24 May
$249pp
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
22 May - 26 May
$268pp
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
23 May - 2 Jun
$269pp
BDL
Hartford Bradley Intl
Multiple 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
3:01 am - 4:49 am
Major Airline
Nonstop
2h 48m
BDL - ORD
Major Airline
$103
StudentUniverse
2:35 pm - 6:26 pm
American Airlines
1 Stop
4h 51m
HVN - ORD
American Airlines
1:35 pm - 7:20 pm
Delta
1 Stop
6h 45m
BDL - MDW
Delta
$139
Delta

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

Are flight prices decreasing from Connecticut to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Connecticut and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

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 American Airlines, United Airlines, and Delta 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 Frontier for just $185, but on average you can expect to pay $224.

Are there nonstop flights from Connecticut to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Connecticut to Chicago under $300. A good price for a nonstop flight from Connecticut to Chicago is less than $322.

Are there last-minute flights available from Connecticut to Chicago for under $300?

There are currently 20+ open flights from Connecticut to Chicago within the next 7 days for less than $300.

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

Consider Major Airline, American Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Connecticut to Chicago.

What are the most popular routes from Connecticut to Chicago?

Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Hartford Bradley Intl - Chicago Midway or New Haven Tweed-New Haven - Chicago O'Hare Intl when deciding on the best route from Connecticut to Chicago.

What are the cheapest Flights from Connecticut to Chicago?

Looking at all options, your cheapest flight can be booked for $146. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $214 on average our data indicates $564 when flying from Connecticut to Chicago

What are the most reliable airlines from Connecticut to Chicago?

No one likes to see their flight delayed. When booking a flight from Connecticut to Chicago consider choosing Envoy Air (100%), British Airways (100%) or United Airlines (98%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Connecticut to Chicago?

There are many flights that can get you from Connecticut to Chicago in 2h 35m. Fly via United Airlines, Delta, or American Airlines to get the fastest option. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Connecticut to Chicago round-trip?

Frontier, at $185, was found to be the cheapest airline from Connecticut to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines.

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

$103 is the cheapest one-way deal found within the past few days, from Major Airline. You may also be able to find cheap deals on Spirit Airlines and American Airlines, with prices starting from $104 and $110, respectively.

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
2h 22m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing

New Haven (HVN)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 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
Spirit Airlines
$141 $262 No cancel fee 65%
American Airlines
$100 $345 No cancel fee 71%
Delta
$122 $399 No cancel fee N/A
United Airlines
$192 $411 No cancel fee 69%
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