Find cheap flights from Connecticut to Chicago

Find cheap flights from Connecticut to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Fri 7/31
Fri 8/7
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

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
Read more about JetBlue

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

Airports
Origin
Hartford
$90
only
$90
Destination
Chicago
$90
only
$90
$206
only
$206
Sat, Jul 25
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Mon, Jul 27
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 3 days
Based on null reviews
Mon, Aug 3
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Thu, Aug 6
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 56m
Trip: 4 days
Based on null reviews
Fri, Aug 21
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
7h 10m
Mon, Aug 24
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
6h 58m
Trip: 4 days
Based on null reviews
Mon, Jul 27
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Wed, Jul 29
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 3 days
Based on null reviews
Fri, Jul 31
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
9h 10m
Mon, Aug 3
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 4 days
Based on null reviews
Sat, Jul 25
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Thu, Jul 30
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 6 days
Based on null reviews
Wed, Sep 9
BDL
Bradley Intl Airport
MDW
Chicago Midway Airport
4h 08m
Mon, Sep 14
MDW
Chicago Midway Airport
BDL
Bradley Intl Airport
5h 27m
Trip: 6 days
Based on null reviews
Sun, Aug 9
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Thu, Aug 13
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
11h 41m
Trip: 5 days
Based on null reviews
Mon, Aug 3
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
12h 37m
Wed, Aug 12
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
21h 09m
Trip: 10 days
Based on null reviews
Sun, Jul 26
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Sun, Aug 2
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
17h 36m
Trip: 8 days
Based on null reviews
Sun, Aug 9
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Thu, Aug 13
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
17h 32m
Trip: 5 days
Based on null reviews
Fri, Jul 31
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
28h 27m
Sun, Aug 2
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
16h 23m
Trip: 3 days
Based on null reviews
Thu, Jul 30
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
28h 24m
Sun, Aug 2
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 4 days
Based on null reviews
Thu, Aug 13
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
10h 19m
Wed, Aug 19
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
21h 09m
Trip: 7 days
Based on null reviews
Sun, Jul 26
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
25h 09m
Wed, Jul 29
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
20h 27m
Trip: 4 days
Based on null reviews
Thu, Aug 20
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
10h 19m
Sun, Aug 23
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
21h 09m
Trip: 4 days
Based on null reviews
Fri, Aug 21
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Sun, Aug 30
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
21h 09m
Trip: 10 days
Based on null reviews
Sun, Jul 26
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
28h 38m
Sun, Aug 2
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
14h 24m
Trip: 8 days
Based on null reviews
Mon, Sep 28
BDL
Bradley Intl Airport
MDW
Chicago Midway Airport
5h 18m
Fri, Oct 2
MDW
Chicago Midway Airport
BDL
Bradley Intl Airport
5h 07m
Trip: 5 days
Based on null reviews
Wed, Jul 29
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
25h 09m
Sat, Aug 15
ORD
Chicago O'Hare Airport
BDL
Bradley Intl Airport
27h 18m
Trip: 18 days
Based on null reviews

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

Airports
Origin
Hartford
$32
only
$32
Destination
Chicago
$32
only
$32
$103
only
$103
Mon, Aug 3
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
10h 14m
Based on null reviews
Mon, Aug 3
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
13h 46m
Based on null reviews
Sun, Aug 16
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
7h 10m
Based on null reviews
Thu, Aug 6
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
10h 22m
Based on null reviews
Mon, Aug 24
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Based on null reviews
Fri, Jul 31
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
9h 10m
Based on null reviews
Sun, Aug 23
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
2h 37m
Based on null reviews
Mon, Jul 27
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
25h 09m
Based on null reviews
Sat, Sep 12
BDL
Bradley Intl Airport
MDW
Chicago Midway Airport
6h 40m
Based on null reviews
Sat, Aug 8
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Based on null reviews
Mon, Aug 17
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
9h 05m
Based on null reviews
Fri, Jul 24
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 10m
Based on null reviews
Fri, Aug 7
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
10h 37m
Based on null reviews
Thu, Aug 13
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Based on null reviews
Sat, Aug 8
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
7h 10m
Based on null reviews
Mon, Aug 17
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
9h 05m
Based on null reviews
Thu, Aug 6
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
18h 26m
Based on null reviews
Thu, Aug 13
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
15h 39m
Based on null reviews
Sun, Aug 23
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
6h 29m
Based on null reviews
Sat, Aug 22
BDL
Bradley Intl Airport
ORD
Chicago O'Hare Airport
30h 01m
Based on null reviews
*
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 and someone from our team will get back to you promptly.

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