Find Cheap Flights from Hartford to Chicago (HFD - CHI)

Flights overview

Useful information for finding cheap flights from Hartford to Chicago and booking your next trip

Cheapest round-trip flights	$248	Frontier 1 stop 11 hr Thu, Jul 16 — Mon, Jul 20	The cheapest round-trip flight from Hartford to Chicago is currently $248
Cheapest one-way flight	$112	JetBlue 1 stop 9 hr Wed, May 27	The cheapest one-way flight from Hartford to Chicago is currently $112
Cheapest nonstop flights	$355	Southwest Nonstop 3 hr Thu, May 28 — Mon, Jun 1	The cheapest nonstop round-trip flight from Hartford to Chicago is currently $355
Last-minute weekend getaway	$650	Frontier 1 stop 29 hr Sat, May 9 — Mon, May 11	The cheapest last-minute weekend getaway from Hartford to Chicago is currently $650
Cheapest business class flights	$605	American Nonstop 4 hr Sat, May 30 — Mon, Jun 1	The cheapest business class round-trip flight from Hartford to Chicago is currently $605

Fastest flight	2 hr 20 min	The fastest nonstop flight from Hartford to Chicago takes 2 hr 20 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Hartford to Chicago is typically October. The most expensive month to fly is typically March.

October Cheapest	Typical prices: $145–385
March Most expensive	Typical prices: $265–450

Popular airlines from Hartford to Chicago

Southwest

Nonstop

from $355

Typical price: $270–590

18 weekly nonstop flights

BDL - MDW Every day

1621 weekly connecting flights

BDL - MDW, ORD Every day
American

Nonstop

from $355

Typical price: $255–590

28 weekly nonstop flights

BDL - ORD Every day

521 weekly connecting flights

BDL - ORD Every day
United

Nonstop

from $355

Typical price: $245–570

27 weekly nonstop flights

BDL - ORD Every day

369 weekly connecting flights

BDL - ORD Every day
Delta

from $375

Typical price: $300–660

514 weekly connecting flights

BDL - MDW, ORD Every day
JetBlue

from $239

Typical price: $385–810

24 weekly connecting flights

BDL - ORD Every day
Frontier

from $250

Typical price: $200–590

10 weekly connecting flights

BDL - MDW, ORD Every Mon, Fri, Sat, Sun

Popular airports near Hartford

Bradley International Airport (BDL)

Hartford United States 19 min 12 mi
John F. Kennedy International Airport (JFK)

New York United States 2 hr 5 min 96 mi
Boston Logan International Airport (BOS)

Boston United States 1 hr 40 min 94 mi
Newark Liberty International Airport (EWR)

Newark United States 2 hr 17 min 107 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Hartford to Chicago

The cheapest flights from Hartford to Chicago are usually in October. Typical ticket prices in October range from $145 to $385.

The cheapest round-trip flight from Hartford to Chicago recently found on Google Flights was with Frontier from $248. The cheapest one-way flight was with JetBlue from $112.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest American flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest United flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest Delta flight from Hartford to Chicago is $375, flying from May 28 to Jun 1.
The cheapest JetBlue flight from Hartford to Chicago is $239, flying from May 30 to Jun 1.
The cheapest Frontier flight from Hartford to Chicago is $250, flying from Jul 9 to Jul 12.

The cheapest round-trip flight from Hartford to Chicago starts at $248 from Thu, Jul 16 to Mon, Jul 20. The cheapest one-way flight starts at $112 and departs on Wed, May 27.

2 hr 20 min is the shortest flight time from Hartford to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Hartford to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Hartford to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Hartford to Chicago.

In terms of nonstop flights, American is the most popular. American offers 28 nonstop flights and 521 connecting flights per week. American flies from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 18 nonstop flights and 1,621 connecting flights per week. Southwest flies from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Hartford to Chicago are:

United offers 27 nonstop flights and 369 connecting flights per week. United flies from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD) .
Delta offers 514 connecting flights per week. Delta flies from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
JetBlue offers 24 connecting flights per week. JetBlue flies from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD) .
Frontier offers 10 connecting flights per week. Frontier flies from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Hartford and Chicago.

The cheapest round-trip flight from Hartford to Chicago recently found on Google Flights was with Frontier from $248. The cheapest one-way flight was with JetBlue from $112.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest American flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest United flight from Hartford to Chicago is $355, flying from May 28 to Jun 1.
The cheapest Delta flight from Hartford to Chicago is $375, flying from May 28 to Jun 1.
The cheapest JetBlue flight from Hartford to Chicago is $239, flying from May 30 to Jun 1.
The cheapest Frontier flight from Hartford to Chicago is $250, flying from Jul 9 to Jul 12.

Southwest, American and United fly direct from Hartford to Chicago.

There are 18 Southwest direct flights from Hartford to Chicago per week. Flights are available every day.
There are 28 American direct flights from Hartford to Chicago per week. Flights are available every day.
There are 27 United direct flights from Hartford to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Hartford and Chicago at price $650 is offered by Frontier from Sat, May 9 to Mon, May 11.

Southwest, American and United fly direct from Hartford to Chicago.

There are 18 Southwest direct flights from Hartford to Chicago per week. Flights are available every day.
There are 28 American direct flights from Hartford to Chicago per week. Flights are available every day.
There are 27 United direct flights from Hartford to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Hartford to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Hartford and Chicago start at $355 from Thu, May 28 to Mon, Jun 1 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Hartford to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Hartford and Chicago start at $605 from Sat, May 30 to Mon, Jun 1 with American.

The cheapest economy class round-trip flights between Hartford and Chicago start at $248 from Thu, Jul 16 to Mon, Jul 20.

To book business class trips from Hartford to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Hartford and Chicago starts at $650 from Sat, May 9 to Mon, May 11 with Frontier.

The cheapest last-minute deal between Hartford and Chicago at price $650 is offered by Frontier from Sat, May 9 to Mon, May 11.

To find last-minute flight deals from Hartford to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.