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

Delta, JetBlue, and Frontier 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 October 2025, there are 20 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 6:00AM, with 52% of flights taking off in the afternoon.

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

As of October 2025, 144 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Tue, with 15% of weekly flights taking off on this day.

What airlines fly to Chicago?

American Airlines, Southwest and United Airlines 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 83% 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.

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 October 2025, 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.

$99 Cheap Flights from Hartford to Chicago in 2025/26

Q: 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 $219 to $441. The lowest price recently found on this route was $202.

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 7:50 pmBDL-ORD

2h 50mnonstop

8:17 am - 11:34 amORD-BDL

2h 17mnonstop

$202American Airlines

Find Deal

Tue, Nov 11 - Thu, Nov 13

7:10 pm - 10:50 amBDL-ORD

16h 40m1 stop

5:25 am - 9:55 pmORD-BDL

15h 30m2 stops

$208Multiple Airlines

Find Deal

Fri, Oct 31 - Sun, Nov 2

6:00 am - 1:10 pmBDL-ORD

8h 10m1 stop

2:05 pm - 11:48 pmORD-BDL

8h 43m1 stop

$218JetBlue

Find Deal

Thu, Jan 22 - Tue, Jan 27

7:36 pm - 9:22 pmBDL-MDW

26h 46m1 stop

10:12 am - 2:12 pmMDW-BDL

27h 00m1 stop

$220Frontier

Find Deal

Fri, Nov 14 - Sun, Nov 16

9:10 am - 3:55 pmBDL-MDW

7h 45m1 stop

9:30 am - 12:35 pmMDW-BDL

2h 05mnonstop

$222Southwest

Find Deal

Tue, Oct 28 - Thu, Oct 30

6:17 pm - 8:11 pmBDL-ORD

2h 54mnonstop

11:01 am - 2:11 pmORD-BDL

2h 10mnonstop

$225United Airlines

Find Deal

Tue, Nov 4 - Sat, Nov 8

1:20 pm - 2:45 pmBDL-MDW

2h 25mnonstop

12:50 pm - 3:50 pmMDW-BDL

2h 00mnonstop

$225Southwest

Find Deal

Thu, Oct 30 - Sat, Nov 1

6:10 am - 8:02 amBDL-ORD

2h 52mnonstop

8:58 am - 12:15 pmORD-BDL

2h 17mnonstop

$227United Airlines

Find Deal

Tue, Nov 11 - Thu, Nov 13

8:31 pm - 11:17 amBDL-MDW

15h 46m1 stop

11:57 am - 10:46 amMDW-BDL

21h 49m1 stop

$227Frontier

Find Deal

Thu, Oct 23 - Sun, Oct 26

7:10 am - 8:52 pmBDL-ORD

14h 42m1 stop

6:45 am - 11:59 pmORD-BDL

16h 14m1 stop

$236JetBlue

Find Deal

Sat, Nov 15 - Sun, Nov 16

American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

American Airlines

Nov 11

BDL6:00 pmHartford Bradley Intl

2h 50m

ORD7:50 pmChicago O'Hare Intl

Nov 13

ORD8:17 amChicago O'Hare Intl

2h 17m

BDL11:34 amHartford Bradley Intl

$202

Find similar

American Airlines

Dec 17

BDL6:07 amHartford Bradley Intl

3h 07m

ORD8:14 amChicago O'Hare Intl

Jan 18

ORD8:19 amChicago O'Hare Intl

2h 19m

BDL11:38 amHartford Bradley Intl

$215

Find similar

American Airlines

Nov 24

BDL6:00 pmHartford Bradley Intl

2h 50m

ORD7:50 pmChicago O'Hare Intl

Nov 26

ORD5:00 amChicago O'Hare Intl

5h 02m

1 stop

BDL11:02 amHartford Bradley Intl

$235

Find similar

JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

JetBlue

Jan 22

BDL6:00 amHartford Bradley Intl

8h 10m

1 stop

ORD1:10 pmChicago O'Hare Intl

Jan 27

ORD2:05 pmChicago O'Hare Intl

8h 43m

1 stop

BDL11:48 pmHartford Bradley Intl

$218

Find similar

JetBlue

Nov 15

BDL7:10 amHartford Bradley Intl

14h 42m

1 stop

ORD8:52 pmChicago O'Hare Intl

Nov 16

ORD6:45 amChicago O'Hare Intl

16h 14m

1 stop

BDL11:59 pmHartford Bradley Intl

$236

Find similar

JetBlue

Dec 11

BDL7:02 amHartford Bradley Intl

15h 50m

1 stop

ORD9:52 pmChicago O'Hare Intl

Dec 15

ORD7:00 amChicago O'Hare Intl

15h 01m

1 stop

BDL11:01 pmHartford Bradley Intl

$237

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 11/11

6:00 pm-7:50 pm

Nonstop2h 50m

Chicago O'Hare Intl

Thu 11/13

8:17 am-11:34 am

Nonstop2h 17m

$202

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 10/31

7:10 pm-10:50 am

1 stop16h 40m

Chicago O'Hare Intl

Sun 11/2

5:25 am-9:55 pm

2 stops15h 30m

$208

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 1/22

6:00 am-1:10 pm

1 stop8h 10m

Chicago O'Hare Intl

Tue 1/27

2:05 pm-11:48 pm

1 stop8h 43m

$218

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 11/14

7:36 pm-9:22 pm

1 stop26h 46m

Chicago Midway

Sun 11/16

10:12 am-2:12 pm

1 stop27h 00m

$220

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 10/28

9:10 am-3:55 pm

1 stop7h 45m

Chicago Midway

Thu 10/30

9:30 am-12:35 pm

Nonstop2h 05m

$222

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 11/4

6:17 pm-8:11 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sat 11/8

11:01 am-2:11 pm

Nonstop2h 10m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/30

1:20 pm-2:45 pm

Nonstop2h 25m

Chicago Midway

Sat 11/1

12:50 pm-3:50 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 11/11

6:10 am-8:02 am

Nonstop2h 52m

Chicago O'Hare Intl

Thu 11/13

8:58 am-12:15 pm

Nonstop2h 17m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/23

8:31 pm-11:17 am

1 stop15h 46m

Chicago Midway

Sun 10/26

11:57 am-10:46 am

1 stop21h 49m

$227

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 11/15

7:10 am-8:52 pm

1 stop14h 42m

Chicago O'Hare Intl

Sun 11/16

6:45 am-11:59 pm

1 stop16h 14m

$236

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?

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 $301. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Hartford to Chicago during October average around $306.

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

Fly from Hartford Bradley Intl to Chicago Midway for the best Hartford Bradley Intl - Chicago flight prices

How far in advance should I book a flight 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 $369 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 $305 on momondo.

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

There are 4 cabin classes available to choose from on Hartford Bradley Intl 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 October 2025, prices for Hartford to Chicago flights are approximately 1% 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	$177
Fastest flight time	2h 25m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Hartford in the past 72 hours is $177. The best round-trip flight deal from Hartford to Chicago found on momondo in the last 72 hours is $310.

The fastest flight from Hartford to Chicago takes 2h 25m

Direct flights go from Hartford to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

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 25m.
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 October 2025, 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 31.11% of the total bookings. Other popular models include Airbus A320-100/200 with 13.66%, Embraer 175 with 13.26%, and Embraer 175 (Enhanced Winglets) with 9.43%.
What is the most popular airline from Hartford to Chicago?
Based on momondo bookings for flights between Hartford and Chicago, the leading airline is American Airlines, making up 41% of the total bookings. Other popular airlines include United Airlines with 31%, Southwest with 24%, and Frontier 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
Frontier	PriceFrom $97	Free Cancellation	Rating 5.8 3,143 reviews	Search Frontier flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 7,969 reviews	Search Delta flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,237 reviews	Search Southwest flights
American Airlines	PriceFrom $190	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 8,968 reviews	Search United Airlines flights

Southwest Flights From Hartford to Chicago
Southwest flies from Hartford to Chicago around 14 times per week, with 4,237 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Hartford to Chicago in the last 72 hours was $177 (round-trip), much lower than the average airfare cost of $379 for Southwest flights on this route.
United Airlines Flights From Hartford to Chicago
Across 8,968 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Hartford to Chicago about 26 times each week, with ticket deals ranging from $227 to $433. Price data is based on momondo searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

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.

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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Dallasfrom $60

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Flights to Denverfrom $53

Cheap flights from Hartford to Chicago from $99

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 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

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Cheap last minute flights

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American Airlines flights from Hartford to Chicago

Our best American Airlines deals on Hartford to Chicago flight tickets

JetBlue flights from Hartford to Chicago

Our best JetBlue deals on Hartford to Chicago flight tickets

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Use the filters below to find and compare flights from Hartford to Chicago that are best for you.

See travel insights to Chicago from

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

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

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 $301. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Hartford to Chicago during October average around $306.

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

Fly from Hartford Bradley Intl to Chicago Midway for the best Hartford Bradley Intl - Chicago flight prices

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

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

There are 4 cabin classes available to choose from on Hartford Bradley Intl 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 October 2025, prices for Hartford to Chicago flights are approximately 1% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

As of October 2025, there are 20 flights per day flying from Hartford to Chicago. The most common time of day flights depart is 6:00AM, with 52% of flights taking off in the afternoon.

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

As of October 2025, 144 flights take off from Hartford and land in Chicago each week. The most common flight departure day for this route is Tue, with 15% of weekly flights taking off on this day.

When to book flights from Hartford to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Hartford Bradley Intl to Chicago by plane?

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

How many operators does momondo search 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?

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

What is the most popular plane model from Hartford to Chicago?

What is the most popular airline 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

Southwest Flights From Hartford to Chicago

United Airlines Flights From Hartford to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

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