Cheap Flights from Connecticut to Chicago from $32

Q: How does KAYAK find such low prices on flights from Connecticut to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Connecticut to Chicago. Visit our flight page for the latest deals!

Q: How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Connecticut is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!

Q: What is the Hacker Fare option on flights from Connecticut to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Connecticut with another airline. Visit our flight page for the latest deals!

Q: What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!

Good to know

Low season	March	Best time to beat the crowds with an average 2% drop in price.
High season	June	Most popular time to fly with an average 7% increase in price.
Average price of a round-trip	$311	(avg. price over the last 2 weeks)
Good deal for a round-trip	$145	or less

FAQs for booking Connecticut to Chicago flights

How does KAYAK find such low prices on flights from Connecticut to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago?

What is the Hacker Fare option on flights from Connecticut to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago?

Top airlines flying from Connecticut to Chicago

Scores according to KAYAK customer reviews

8.2

JetBlue

Overall score based on 19,204 reviews

8.3

Boarding

8.3

Comfort

8.6

Crew

7.9

Entertainment

7.8

Food

Airline reviews

Book cheap flights from Connecticut to Chicago (round-trip)

Airports

Origin

Destination

Spirit Airlines

Sat, Jul 25

15h 10m

Mon, Jul 27

14h 24m

$90

Trip: 3 days

Based on null reviews

Multiple Airlines

Mon, Aug 3

15h 10m

Thu, Aug 6

14h 56m

$93

Trip: 4 days

Based on null reviews

JetBlue

Fri, Aug 21

7h 10m

Mon, Aug 24

6h 58m

$114

Trip: 4 days

Based on null reviews

Spirit Airlines

Mon, Jul 27

15h 10m

Wed, Jul 29

14h 24m

$91

Trip: 3 days

Based on null reviews

Multiple Airlines

Fri, Jul 31

9h 10m

Mon, Aug 3

14h 24m

$94

Trip: 4 days

Based on null reviews

Spirit Airlines

Sat, Jul 25

15h 10m

Thu, Jul 30

14h 24m

$92

Trip: 6 days

Based on null reviews

Delta

Wed, Sep 9

4h 08m

Mon, Sep 14

5h 27m

$206

Trip: 6 days

Based on null reviews

Multiple Airlines

Sun, Aug 9

18h 26m

Thu, Aug 13

11h 41m

$95

Trip: 5 days

Based on null reviews

Multiple Airlines

Mon, Aug 3

12h 37m

Wed, Aug 12

21h 09m

$96

Trip: 10 days

Based on null reviews

Multiple Airlines

Sun, Jul 26

15h 10m

Sun, Aug 2

17h 36m

$97

Trip: 8 days

Based on null reviews

Spirit Airlines

Sun, Aug 9

18h 26m

Thu, Aug 13

17h 32m

$108

Trip: 5 days

Based on null reviews

Multiple Airlines

Fri, Jul 31

28h 27m

Sun, Aug 2

16h 23m

$98

Trip: 3 days

Based on null reviews

Spirit Airlines

Thu, Jul 30

28h 24m

Sun, Aug 2

14h 24m

$110

Trip: 4 days

Based on null reviews

Multiple Airlines

Thu, Aug 13

10h 19m

Wed, Aug 19

21h 09m

$99

Trip: 7 days

Based on null reviews

Spirit Airlines

Sun, Jul 26

25h 09m

Wed, Jul 29

20h 27m

$111

Trip: 4 days

Based on null reviews

Multiple Airlines

Thu, Aug 20

10h 19m

Sun, Aug 23

21h 09m

$101

Trip: 4 days

Based on null reviews

Spirit Airlines

Fri, Aug 21

18h 26m

Sun, Aug 30

21h 09m

$115

Trip: 10 days

Based on null reviews

Multiple Airlines

Sun, Jul 26

28h 38m

Sun, Aug 2

14h 24m

$102

Trip: 8 days

Based on null reviews

Delta

Mon, Sep 28

5h 18m

Fri, Oct 2

5h 07m

$216

Trip: 5 days

Based on null reviews

Multiple Airlines

Wed, Jul 29

25h 09m

Sat, Aug 15

27h 18m

$103

Trip: 18 days

Based on null reviews

Book cheap flights from Connecticut to Chicago (one-way)

Airports

Origin

Destination

Spirit Airlines

Mon, Aug 3

10h 14m

$32

Based on null reviews

Multiple Airlines

Mon, Aug 3

13h 46m

$34

Based on null reviews

JetBlue

Sun, Aug 16

7h 10m

$57

Based on null reviews

Multiple Airlines

Thu, Aug 6

10h 22m

$38

Based on null reviews

Spirit Airlines

Mon, Aug 24

18h 26m

$41

Based on null reviews

Multiple Airlines

Fri, Jul 31

9h 10m

$39

Based on null reviews

Major Airline

Sun, Aug 23

2h 37m

$87

Based on null reviews

Spirit Airlines

Mon, Jul 27

25h 09m

$42

Based on null reviews

Delta

Sat, Sep 12

6h 40m

$103

Based on null reviews

Spirit Airlines

Sat, Aug 8

18h 26m

$43

Based on null reviews

Multiple Airlines

Mon, Aug 17

9h 05m

$47

Based on null reviews

Spirit Airlines

Fri, Jul 24

15h 10m

$44

Based on null reviews

Multiple Airlines

Fri, Aug 7

10h 37m

$48

Based on null reviews

Spirit Airlines

Thu, Aug 13

18h 26m

$45

Based on null reviews

JetBlue

Sat, Aug 8

7h 10m

$72

Based on null reviews

Multiple Airlines

Mon, Aug 17

9h 05m

$50

Based on null reviews

Spirit Airlines

Thu, Aug 6

18h 26m

$46

Based on null reviews

Multiple Airlines

Thu, Aug 13

15h 39m

$52

Based on null reviews

Major Airline

Sun, Aug 23

6h 29m

$90

Based on null reviews

Multiple Airlines

Sat, Aug 22

30h 01m

$53

Based on null reviews

Flights to Chicago

Return flight deals:

Chicago - Connecticut

Cabin classes:

First

$388

Business

Prem Econ

$106

Economy

Browse origins:

$91

Hartford

$163

New Haven

Browse destinations:

$206

Chicago Midway Airport

$91

Chicago O'Hare Airport

Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Find cheap flights from Connecticut to Chicago

Good to know

Low season

High season

Average price of a round-trip

Good deal for a round-trip

FAQs for booking Connecticut to Chicago flights

How does KAYAK find such low prices on flights from Connecticut to Chicago?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago?

What is the Hacker Fare option on flights from Connecticut to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago?

Top airlines flying from Connecticut to Chicago

Book cheap flights from Connecticut to Chicago (round-trip)

Book cheap flights from Connecticut to Chicago (one-way)

Flights to Chicago

Site