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

Flights overview

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

Cheapest round-trip flights	$172	American Nonstop 3 hr Sat, May 30 — Sun, May 31	The cheapest round-trip flight from Chicago to Boston is currently $172
Cheapest one-way flight	$84	JetBlue Nonstop 3 hr Wed, May 27	The cheapest one-way flight from Chicago to Boston is currently $84
Last-minute weekend getaway	$232	Frontier 1 stop 11 hr Fri, May 8 — Sun, May 10	The cheapest last-minute weekend getaway from Chicago to Boston is currently $232
Cheapest business class flights	$428	American Nonstop 3 hr Sat, May 30 — Sun, May 31	The cheapest business class round-trip flight from Chicago to Boston is currently $428

Fastest flight	2 hr 10 min	The fastest nonstop flight from Chicago to Boston takes 2 hr 10 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 Chicago to Boston is typically September. The most expensive month to fly is typically May.

September Cheapest	Typical prices: $105–180
May Most expensive	Typical prices: $140–200

Popular airlines from Chicago to Boston

American

Nonstop

from $172

Typical price: $135–270

69 weekly nonstop flights

ORD - BOS Every day

420 weekly connecting flights

ORD - BOS Every day
United

Nonstop

from $172

Typical price: $130–275

59 weekly nonstop flights

ORD - BOS Every day

149 weekly connecting flights

ORD - BOS Every day
Delta

Nonstop

from $172

Typical price: $155–345

27 weekly nonstop flights

ORD - BOS Every day

1089 weekly connecting flights

MDW, ORD - BOS Every day
Southwest

Nonstop

from $187

Typical price: $135–305

28 weekly nonstop flights

MDW - BOS Every day

937 weekly connecting flights

MDW, ORD - BOS Every day
JetBlue

Nonstop

from $177

Typical price: $145–375

11 weekly nonstop flights

ORD - BOS Every day

10 weekly connecting flights

ORD - BOS Every day
Frontier

from $224

Typical price: $200–590

42 weekly connecting flights

MDW, ORD - BOS Every day

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

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 37 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

Frequently asked questions about flying from Chicago to Boston

The cheapest flights from Chicago to Boston are usually in September. Typical ticket prices in September range from $105 to $180.

The cheapest round-trip flight from Chicago to Boston recently found on Google Flights was with American from $172. The cheapest one-way flight was with JetBlue from $84.

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

The cheapest American flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest United flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest Delta flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest Southwest flight from Chicago to Boston is $187, flying from May 29 to May 31.
The cheapest JetBlue flight from Chicago to Boston is $177, flying from May 28 to May 31.
The cheapest Frontier flight from Chicago to Boston is $224, flying from Jul 18 to Jul 19.

The cheapest round-trip flight from Chicago to Boston starts at $172 from Sat, May 30 to Sun, May 31. The cheapest one-way flight starts at $84 and departs on Wed, May 27.

2 hr 10 min is the shortest flight time from Chicago to Boston.

Boston is a year-round destination with a 4-season climate. Spring and fall feature generally mild weather, although snow sometimes falls in early spring (Apr). Summer can be humid. Foliage season (mid-Sep–Nov) attracts the largest crowds. Patriots Day (3rd Mon of Apr) commemorates the start of the Revolutionary War and coincides with the famed Boston Marathon. Summer festivals include Boston Harborfest, the city’s weeklong 4th of July party, and Italian-American celebrations in the North End (late Jul–Aug).

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Boston.
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 Chicago to Boston 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 Chicago to Boston.

In terms of nonstop flights, American is the most popular. American offers 69 nonstop flights and 420 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .

In terms of flights, Delta is the most popular. Delta offers 27 nonstop flights and 1,089 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .

Other popular airlines flying from Chicago to Boston are:

United offers 59 nonstop flights and 149 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .
Southwest offers 28 nonstop flights and 937 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .
JetBlue offers 11 nonstop flights and 10 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .
Frontier offers 42 connecting flights per week. Frontier flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .

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

The cheapest round-trip flight from Chicago to Boston recently found on Google Flights was with American from $172. The cheapest one-way flight was with JetBlue from $84.

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

The cheapest American flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest United flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest Delta flight from Chicago to Boston is $172, flying from May 30 to May 31.
The cheapest Southwest flight from Chicago to Boston is $187, flying from May 29 to May 31.
The cheapest JetBlue flight from Chicago to Boston is $177, flying from May 28 to May 31.
The cheapest Frontier flight from Chicago to Boston is $224, flying from Jul 18 to Jul 19.

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

There are 69 American direct flights from Chicago to Boston per week. Flights are available every day.
There are 59 United direct flights from Chicago to Boston per week. Flights are available every day.
There are 27 Delta direct flights from Chicago to Boston per week. Flights are available every day.
There are 28 Southwest direct flights from Chicago to Boston per week. Flights are available every day.
There are 11 JetBlue direct flights from Chicago to Boston 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 Chicago and Boston at price $232 is offered by Frontier from Fri, May 8 to Sun, May 10.

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

There are 69 American direct flights from Chicago to Boston per week. Flights are available every day.
There are 59 United direct flights from Chicago to Boston per week. Flights are available every day.
There are 27 Delta direct flights from Chicago to Boston per week. Flights are available every day.
There are 28 Southwest direct flights from Chicago to Boston per week. Flights are available every day.
There are 11 JetBlue direct flights from Chicago to Boston 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 Chicago to Boston on a daily basis.

The cheapest direct (nonstop) round-trip flights between Chicago and Boston start at $172 from Sat, May 30 to Sun, May 31 with American.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Boston, 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 Chicago and Boston start at $428 from Sat, May 30 to Sun, May 31 with American.

The cheapest economy class round-trip flights between Chicago and Boston start at $172 from Sat, May 30 to Sun, May 31.

To book business class trips from Chicago to Boston, 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 Chicago and Boston starts at $232 from Fri, May 8 to Sun, May 10 with Frontier.

The cheapest last-minute deal between Chicago and Boston at price $232 is offered by Frontier from Fri, May 8 to Sun, May 10.

To find last-minute flight deals from Chicago to Boston, 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.