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	$117	American Nonstop 3 hr Sat, Dec 13 — Sun, Dec 14	The cheapest round-trip flight from Chicago to Boston is currently $117
Cheapest one-way flight	$55	Frontier 1 stop 8 hr Wed, Jan 7	The cheapest one-way flight from Chicago to Boston is currently $55
Last-minute weekend getaway	$148	United Nonstop 3 hr Thu, Nov 20 — Sun, Nov 23	The cheapest last-minute weekend getaway from Chicago to Boston is currently $148
Cheapest business class flights	$343	American Nonstop 3 hr Thu, Dec 4 — Sun, Dec 7	The cheapest business class round-trip flight from Chicago to Boston is currently $343

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 July.

September Cheapest	Typical prices: $105–180
July Most expensive	Typical prices: $135–190

Popular airlines from Chicago to Boston

American

Nonstop

from $117

Typical price: $145–285

60 weekly nonstop flights

ORD - BOS Every day

412 weekly connecting flights

ORD - BOS Every day
United

Nonstop

from $117

Typical price: $135–295

54 weekly nonstop flights

ORD - BOS Every day

130 weekly connecting flights

ORD - BOS Every day
Delta

Nonstop

from $137

Typical price: $155–350

27 weekly nonstop flights

ORD - BOS Every day

1139 weekly connecting flights

MDW, ORD - BOS Every day
Southwest

Nonstop

from $122

Typical price: $145–310

17 weekly nonstop flights

MDW - BOS Every day

723 weekly connecting flights

MDW, ORD - BOS Every day
JetBlue

Nonstop

from $122

Typical price: $160–380

11 weekly nonstop flights

ORD - BOS Every day

12 weekly connecting flights

ORD - BOS Every day
Frontier

from $110

Typical price: $155–430

32 weekly connecting flights

MDW, ORD - BOS Every Tue, Wed, Thu, Fri, Sat, Sun

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 31 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 26 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 28 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 38 min 184 mi
LaGuardia Airport (LGA)

New York United States 3 hr 27 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

When are the cheapest days to fly 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.

Which airlines provide the cheapest flights from Chicago to Boston?

The cheapest round-trip flight from Chicago to Boston recently found on Google Flights was with American from $117. The cheapest one-way flight was with Frontier from $55.

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

The cheapest American flight from Chicago to Boston is $117, flying from Dec 13 to Dec 14.
The cheapest United flight from Chicago to Boston is $117, flying from Dec 13 to Dec 14.
The cheapest Delta flight from Chicago to Boston is $137, flying from Jan 23 to Jan 25.
The cheapest Southwest flight from Chicago to Boston is $122, flying from Dec 11 to Dec 14.
The cheapest JetBlue flight from Chicago to Boston is $122, flying from Dec 11 to Dec 14.
The cheapest Frontier flight from Chicago to Boston is $110, flying from Jan 22 to Jan 26.

What are the cheapest flights from Chicago to Boston?

The cheapest round-trip flight from Chicago to Boston starts at $117 from Sat, Dec 13 to Sun, Dec 14. The cheapest one-way flight starts at $55 and departs on Wed, Jan 7.

How long does it take to fly from Chicago to Boston?

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

When should you fly to Boston, United States?

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).

How do I find cheap dates to fly from Chicago to Boston?

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 is the best airline to fly from Chicago to Boston?

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 60 nonstop flights and 412 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 1,139 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 54 nonstop flights and 130 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .
Southwest offers 17 nonstop flights and 723 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 12 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) .
Frontier offers 32 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.

Which airlines provide the cheapest flights from Chicago to Boston?

The cheapest round-trip flight from Chicago to Boston recently found on Google Flights was with American from $117. The cheapest one-way flight was with Frontier from $55.

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

The cheapest American flight from Chicago to Boston is $117, flying from Dec 13 to Dec 14.
The cheapest United flight from Chicago to Boston is $117, flying from Dec 13 to Dec 14.
The cheapest Delta flight from Chicago to Boston is $137, flying from Jan 23 to Jan 25.
The cheapest Southwest flight from Chicago to Boston is $122, flying from Dec 11 to Dec 14.
The cheapest JetBlue flight from Chicago to Boston is $122, flying from Dec 11 to Dec 14.
The cheapest Frontier flight from Chicago to Boston is $110, flying from Jan 22 to Jan 26.

Which airlines have direct flights from Chicago to Boston?

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

There are 60 American direct flights from Chicago to Boston per week. Flights are available every day.
There are 54 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 17 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.

Which airline provides the cheapest last-minute getaway flight from Chicago to Boston?

The cheapest last-minute deal between Chicago and Boston at price $148 is offered by United from Thu, Nov 20 to Sun, Nov 23.

Which airlines have direct flights from Chicago to Boston?

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

There are 60 American direct flights from Chicago to Boston per week. Flights are available every day.
There are 54 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 17 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.

When are direct flights from Chicago to Boston available?

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

What are the cheapest direct flights from Chicago to Boston?

The cheapest direct (nonstop) round-trip flights between Chicago and Boston start at $117 from Sat, Dec 13 to Sun, Dec 14 with American.

How can I find nonstop flights from Chicago to Boston?

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.

What are the cheapest business class flights from Chicago to Boston?

The cheapest business class round-trip flights between Chicago and Boston start at $343 from Thu, Dec 4 to Sun, Dec 7 with American.

What are the cheapest economy class flights from Chicago to Boston?

The cheapest economy class round-trip flights between Chicago and Boston start at $117 from Sat, Dec 13 to Sun, Dec 14.

How can I book business class trips from Chicago to Boston?

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.

Are there any last-minute deals from Chicago to Boston next weekend?

The best last-minute getaway deal for the next weekend between Chicago and Boston starts at $148 from Thu, Nov 20 to Sun, Nov 23 with United.

Which airline provides the cheapest last-minute getaway flight from Chicago to Boston?

The cheapest last-minute deal between Chicago and Boston at price $148 is offered by United from Thu, Nov 20 to Sun, Nov 23.

How can I find last-minute flight deals from Chicago to Boston?

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.