Find Cheap Flights from Boston to Chicago (BOS - CHI)

Flights overview

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

Cheapest round-trip flights	$186	United Nonstop 3 hr Sat, May 30 — Sun, May 31	The cheapest round-trip flight from Boston to Chicago is currently $186
Cheapest one-way flight	$84	Southwest Nonstop 3 hr Wed, May 27	The cheapest one-way flight from Boston to Chicago is currently $84
Last-minute weekend getaway	$257	United Nonstop 3 hr Thu, May 14 — Sun, May 17	The cheapest last-minute weekend getaway from Boston to Chicago is currently $257
Cheapest business class flights	$440	American Nonstop 3 hr Sat, May 30 — Sun, May 31	The cheapest business class round-trip flight from Boston to Chicago is currently $440

Fastest flight	2 hr 30 min	The fastest nonstop flight from Boston to Chicago takes 2 hr 30 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 Boston to Chicago is typically September. The most expensive month to fly is typically May.

September Cheapest	Typical prices: $100–140
May Most expensive	Typical prices: $155–220

Popular airlines from Boston to Chicago

American

Nonstop

from $186

Typical price: $135–275

66 weekly nonstop flights

BOS - ORD Every day

421 weekly connecting flights

BOS - ORD Every day
United

Nonstop

from $186

Typical price: $130–280

59 weekly nonstop flights

BOS - ORD Every day

146 weekly connecting flights

BOS - ORD Every day
Southwest

Nonstop

from $205

Typical price: $135–310

28 weekly nonstop flights

BOS - MDW Every day

964 weekly connecting flights

BOS - MDW, ORD Every day
Delta

Nonstop

from $247

Typical price: $155–345

27 weekly nonstop flights

BOS - ORD Every day

1013 weekly connecting flights

BOS - MDW, ORD Every day
JetBlue

Nonstop

from $205

Typical price: $145–385

11 weekly nonstop flights

BOS - ORD Every day

10 weekly connecting flights

BOS - ORD Every day
Frontier

from $224

Typical price: $200–610

44 weekly connecting flights

BOS - MDW, ORD Every day

Popular airports near Boston

Boston Logan International Airport (BOS)

Boston United States 12 min 2 mi
John F. Kennedy International Airport (JFK)

New York United States 3 hr 36 min 184 mi
LaGuardia Airport (LGA)

New York United States 3 hr 25 min 181 mi
Rhode Island T.F. Green International Airport (PVD)

Providence United States 1 hr 7 min 47 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 25 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 24 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 Boston to Chicago

The cheapest flights from Boston to Chicago are usually in September. Typical ticket prices in September range from $100 to $140.

The cheapest round-trip flight from Boston to Chicago recently found on Google Flights was with United from $186. The cheapest one-way flight was with Southwest from $84.

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

The cheapest American flight from Boston to Chicago is $186, flying from May 30 to May 31.
The cheapest United flight from Boston to Chicago is $186, flying from May 30 to May 31.
The cheapest Southwest flight from Boston to Chicago is $205, flying from Jul 2 to Jul 5.
The cheapest Delta flight from Boston to Chicago is $247, flying from May 28 to May 31.
The cheapest JetBlue flight from Boston to Chicago is $205, flying from Jul 23 to Jul 27.
The cheapest Frontier flight from Boston to Chicago is $224, flying from Jul 11 to Jul 13.

The cheapest round-trip flight from Boston to Chicago starts at $186 from Sat, May 30 to Sun, May 31. The cheapest one-way flight starts at $84 and departs on Wed, May 27.

2 hr 30 min is the shortest flight time from Boston 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 Boston 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 Boston 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 Boston to Chicago.

In terms of nonstop flights, American is the most popular. American offers 66 nonstop flights and 421 connecting flights per week. American flies from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Delta is the most popular. Delta offers 27 nonstop flights and 1,013 connecting flights per week. Delta flies from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Boston to Chicago are:

United offers 59 nonstop flights and 146 connecting flights per week. United flies from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD) .
Southwest offers 28 nonstop flights and 964 connecting flights per week. Southwest flies from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
JetBlue offers 11 nonstop flights and 10 connecting flights per week. JetBlue flies from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD) .
Frontier offers 44 connecting flights per week. Frontier flies from Boston Logan International Airport (BOS) 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 Boston and Chicago.

The cheapest round-trip flight from Boston to Chicago recently found on Google Flights was with United from $186. The cheapest one-way flight was with Southwest from $84.

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

The cheapest American flight from Boston to Chicago is $186, flying from May 30 to May 31.
The cheapest United flight from Boston to Chicago is $186, flying from May 30 to May 31.
The cheapest Southwest flight from Boston to Chicago is $205, flying from Jul 2 to Jul 5.
The cheapest Delta flight from Boston to Chicago is $247, flying from May 28 to May 31.
The cheapest JetBlue flight from Boston to Chicago is $205, flying from Jul 23 to Jul 27.
The cheapest Frontier flight from Boston to Chicago is $224, flying from Jul 11 to Jul 13.

Southwest, American, United, Delta and JetBlue fly direct from Boston to Chicago.

There are 66 American direct flights from Boston to Chicago per week. Flights are available every day.
There are 59 United direct flights from Boston to Chicago per week. Flights are available every day.
There are 28 Southwest direct flights from Boston to Chicago per week. Flights are available every day.
There are 27 Delta direct flights from Boston to Chicago per week. Flights are available every day.
There are 11 JetBlue direct flights from Boston 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 Boston and Chicago at price $257 is offered by United from Thu, May 14 to Sun, May 17.

Southwest, American, United, Delta and JetBlue fly direct from Boston to Chicago.

There are 66 American direct flights from Boston to Chicago per week. Flights are available every day.
There are 59 United direct flights from Boston to Chicago per week. Flights are available every day.
There are 28 Southwest direct flights from Boston to Chicago per week. Flights are available every day.
There are 27 Delta direct flights from Boston to Chicago per week. Flights are available every day.
There are 11 JetBlue direct flights from Boston 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 Boston to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Boston and Chicago start at $186 from Sat, May 30 to Sun, May 31 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Boston 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 Boston and Chicago start at $440 from Sat, May 30 to Sun, May 31 with American.

The cheapest economy class round-trip flights between Boston and Chicago start at $186 from Sat, May 30 to Sun, May 31.

To book business class trips from Boston 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 Boston and Chicago starts at $257 from Thu, May 14 to Sun, May 17 with United.

The cheapest last-minute deal between Boston and Chicago at price $257 is offered by United from Thu, May 14 to Sun, May 17.

To find last-minute flight deals from Boston 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.