What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Hartford according to our data. American Airlines is the first choice among our users, with 75% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Hartford to Chicago on average per week?

As of August 2026, 135 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.

What is the cheapest airline that flies from Hartford Bradley Intl to Chicago?

JetBlue, Delta, and Southwest are the most popular carriers operating from Hartford Bradley Intl to Chicago

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

As of August 2026, there are 19 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 12:00PM, with 50% of flights taking off at noon.

When did momondo last update prices for flights from Hartford Bradley Intl Airport to Chicago?

Prices for flights from Hartford Bradley Intl Airport to Chicago refresh daily.

How many operators does momondo search for flights from Hartford Bradley Intl Airport to Chicago?

As of August 2026, there are 5 operators available to choose from for flights from Hartford Bradley Intl Airport to Chicago.

How old do you have to be to fly from Hartford Bradley Intl Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Hartford Bradley Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$140 Cheap Flights from Hartford to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hartford to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:10 pm - 8:06 pm

BDL

ORD

2h 56mnonstop

8:20 am - 11:41 am

ORD

BDL

2h 21mnonstop

$277American Airlines

Wed, Jan 13 - Sat, Jan 16

12:32 pm - 2:20 pm

BDL

ORD

2h 48mnonstop

2:04 pm - 5:30 pm

ORD

BDL

2h 26mnonstop

$277American Airlines

Tue, Oct 27 - Sat, Oct 31

6:00 am - 7:46 am

BDL

ORD

2h 46mnonstop

6:19 pm - 9:42 pm

ORD

BDL

2h 23mnonstop

$277United Airlines

Sat, Sep 5 - Sun, Sep 6

12:38 pm - 2:23 pm

BDL

ORD

2h 45mnonstop

7:30 am - 10:49 am

ORD

BDL

2h 19mnonstop

$277United Airlines

Sat, Oct 3 - Tue, Oct 6

8:00 am - 9:20 am

BDL

MDW

2h 20mnonstop

7:10 pm - 10:20 pm

MDW

BDL

2h 10mnonstop

$277Southwest

Thu, Aug 27 - Thu, Sep 3

3:50 pm - 5:15 pm

BDL

MDW

2h 25mnonstop

8:45 am - 12:00 pm

MDW

BDL

2h 15mnonstop

$277Southwest

Sat, Sep 19 - Mon, Sep 21

1:42 pm - 11:27 pm

BDL

ORD

10h 45m

1 stop

12:44 am - 12:47 pm

ORD

BDL

11h 03m

1 stop

$279Frontier

Tue, Aug 25 - Sun, Aug 30

6:25 am - 11:47 am

BDL

ORD

6h 22m

1 stop

6:05 am - 8:00 pm

ORD

BDL

12h 55m

1 stop

$279Multiple Airlines

Thu, Oct 22 - Sun, Oct 25

5:07 pm - 11:44 pm

BDL

ORD

7h 37m

1 stop

5:27 pm - 12:20 am

ORD

BDL

5h 53m

1 stop

$280JetBlue

Thu, Aug 20 - Mon, Aug 24

5:07 pm - 11:44 pm

BDL

ORD

7h 37m

1 stop

2:35 pm - 11:58 pm

ORD

BDL

8h 23m

1 stop

$285JetBlue

Sun, Aug 30 - Fri, Sep 4

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JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

JetBlue

Aug 20

BDL5:07 pmHartford Bradley Intl

7h 37m

1 stop

ORD11:44 pmChicago O'Hare Intl

Aug 24

ORD5:27 pmChicago O'Hare Intl

5h 53m

1 stop

BDL12:20 amHartford Bradley Intl

$280

JetBlue

Aug 12

BDL5:07 pmHartford Bradley Intl

7h 37m

1 stop

ORD11:44 pmChicago O'Hare Intl

Aug 18

ORD2:35 pmChicago O'Hare Intl

8h 23m

1 stop

BDL11:58 pmHartford Bradley Intl

$285

JetBlue

Aug 12

BDL5:07 pmHartford Bradley Intl

7h 37m

1 stop

ORD11:44 pmChicago O'Hare Intl

Aug 14

ORD5:27 pmChicago O'Hare Intl

5h 53m

1 stop

BDL12:20 amHartford Bradley Intl

$287

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

American Airlines

Aug 27

BDL12:11 pmHartford Bradley Intl

2h 50m

ORD2:01 pmChicago O'Hare Intl

Sep 3

ORD7:35 pmChicago O'Hare Intl

2h 19m

BDL10:54 pmHartford Bradley Intl

$278

American Airlines

Sep 5

BDL5:41 pmHartford Bradley Intl

3h 09m

ORD7:50 pmChicago O'Hare Intl

Sep 6

ORD8:10 amChicago O'Hare Intl

2h 26m

BDL11:36 amHartford Bradley Intl

$279

American Airlines

Aug 24

BDL5:41 pmHartford Bradley Intl

3h 09m

ORD7:50 pmChicago O'Hare Intl

Aug 29

ORD8:44 pmChicago O'Hare Intl

2h 14m

BDL11:58 pmHartford Bradley Intl

$283

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 1/13

6:10 pm-8:06 pm

Nonstop2h 56m

Chicago O'Hare Intl

Sat 1/16

8:20 am-11:41 am

Nonstop2h 21m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 10/27

12:32 pm-2:20 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sat 10/31

2:04 pm-5:30 pm

Nonstop2h 26m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 9/5

6:00 am-7:46 am

Nonstop2h 46m

Chicago O'Hare Intl

Sun 9/6

6:19 pm-9:42 pm

Nonstop2h 23m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 10/3

12:38 pm-2:23 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 10/6

7:30 am-10:49 am

Nonstop2h 19m

$277

Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/27

8:00 am-9:20 am

Nonstop2h 20m

Chicago Midway

Thu 9/3

7:10 pm-10:20 pm

Nonstop2h 10m

$277

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 9/19

3:50 pm-5:15 pm

Nonstop2h 25m

Chicago Midway

Mon 9/21

8:45 am-12:00 pm

Nonstop2h 15m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 8/25

1:42 pm-11:27 pm

1 stop10h 45m

Chicago O'Hare Intl

Sun 8/30

12:44 am-12:47 pm

1 stop11h 03m

$279

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 10/22

6:25 am-11:47 am

1 stop6h 22m

Chicago O'Hare Intl

Sun 10/25

6:05 am-8:00 pm

1 stop12h 55m

$279

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 8/20

5:07 pm-11:44 pm

1 stop7h 37m

Chicago O'Hare Intl

Mon 8/24

5:27 pm-12:20 am

1 stop5h 53m

$280

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 8/30

5:07 pm-11:44 pm

1 stop7h 37m

Chicago O'Hare Intl

Fri 9/4

2:35 pm-11:58 pm

1 stop8h 23m

$285

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Hartford to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Hartford and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $303 to $441.
The lowest price recently found on this route was $277.

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Hartford, with most prices found around $336. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Hartford to Chicago during January average around $344.

What is the cheapest Hartford Bradley Intl to Chicago flight route?

Fly from Hartford Bradley Intl to Chicago O'Hare Intl for the best Hartford Bradley Intl - Chicago flight prices

How far in advance should I book a flight from Hartford to Chicago?

You are more likely to see cheaper flights to Chicago from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $411 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hartford for as low as $344 on momondo.

What cabin class options are available on Hartford to Chicago flights?

There are 4 cabin classes available to choose from on Hartford to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hartford to Chicago flights?

No. A direct flight is the cheapest option for a flight between Hartford to Chicago.

How have Hartford to Chicago flight prices changed over time?

As of August 2026, prices for Hartford to Chicago flights are approximately 27% cheaper when compared to flights at the same time last year.

When to book flights from Hartford to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hartford to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Hartford to Chicago (BDL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hartford to Chicago

Best Price Found	$214
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hartford in the past 72 hours is $214. The best round-trip flight deal from Hartford to Chicago found on momondo in the last 72 hours is $383.

The fastest flight from Hartford to Chicago takes 2h 15m

Direct flights go from Hartford to Chicago every day.

There are 3 airports in Chicago. From Hartford there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Hartford to Chicago

How far is Hartford Bradley Intl to Chicago by plane?
Chicago is 768.4 mi away from Hartford Bradley Intl. A reasonable flight in good conditions will take 2h 15m.
When did momondo last update prices for flights from Hartford Bradley Intl Airport to Chicago?
Prices for flights from Hartford Bradley Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Hartford Bradley Intl Airport to Chicago?
As of August 2026, there are 5 operators available to choose from for flights from Hartford Bradley Intl Airport to Chicago.
How old do you have to be to fly from Hartford Bradley Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Hartford Bradley Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Hartford to Chicago?
Based on momondo bookings for flights between Hartford and Chicago, the leading plane model is Boeing 737-800, making up 31.81% of the total bookings. Other popular models include Embraer 175 with 15.83%, Boeing 737-900 with 12.06%, and Embraer 175 (Enhanced Winglets) with 11.86%.
What is the most popular airline from Hartford to Chicago?
Based on momondo bookings for flights between Hartford and Chicago, the leading airline is United Airlines, making up 40% of the total bookings. Other popular airlines include American Airlines with 32%, Southwest with 24%, and JetBlue with 2%.

Best airlines flying from Hartford to Chicago

Compare and see reviews for airlines that fly from Hartford to Chicago with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $84	Free Cancellation	Rating 7.1 3,029 reviews	Search JetBlue flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.8 8,494 reviews	Search Delta flights
American Airlines	PriceFrom $216	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights
United Airlines	PriceFrom $234	Free Cancellation	Rating 7.4 10,062 reviews	Search United Airlines flights
Southwest	PriceFrom $279	Free Cancellation	Rating 8.0 4,229 reviews	Search Southwest flights

Southwest Flights From Hartford to Chicago
Southwest flies from Hartford to Chicago around 8 times per week, with 4,229 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Hartford to Chicago in the last 72 hours was $279 (round-trip), much lower than the average airfare cost of $428 for Southwest flights on this route.
United Airlines Flights From Hartford to Chicago
Across 10,062 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Hartford to Chicago about 28 times each week, with ticket deals ranging from $234 to $439. Price data is based on momondo searches in the last 72 hours.

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Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hartford to Chicago?

Finding the right flight to Chicago from Hartford is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Hartford to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Hartford which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Hartford to Chicago?

Once you have performed a search for Hartford to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Hartford to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Hartford to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Fly into one of these airports located in Chicago

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Cheap flights from Hartford to Chicago from $140

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hartford to Chicago departing on 9/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Hartford to Chicago

What is the typical price of a round-trip flight between Hartford and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest Hartford Bradley Intl to Chicago flight route?

How far in advance should I book a flight from Hartford to Chicago?

What cabin class options are available on Hartford to Chicago flights?

Can stopping save me money on Hartford to Chicago flights?

How have Hartford to Chicago flight prices changed over time?

What is the cheapest airline that flies from Hartford Bradley Intl to Chicago?

What airlines fly to Chicago?

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

How many flights depart from Hartford to Chicago on average per week?

When to book flights from Hartford to Chicago

Cheap Hartford to Chicago (BDL to CHI) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Hartford to Chicago

Best airlines flying from Hartford to Chicago

Compare and see reviews for airlines that fly from Hartford to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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