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Flights from Chicago, IL (CHI-All Airports) to Logan International Airport (BOS)
Flights to Boston
Massachusetts
United States of America
Flights
Expedia.com

Popular airlines from Chicago to Boston, MA (BOS-Logan Intl.)

JetBlue Airways
Delta
American Airlines
United
Alaska Airlines
Frontier Airlines
Southwest Airlines

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Cheap Flights from Chicago to Boston (CHI-BOS)

Prices were available within the past 7 days and start at $101 for one-way flights and $246 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Thu, Dec 3 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$246

Roundtrip

Found 1 hour ago

Select Frontier Airlines flight, departing Thu, Dec 3 from Chicago to Boston, returning Mon, Dec 7, priced at $246 Found 1 hour ago

Thu, Dec 10 - Sat, Dec 12

ORD

Chicago

BOS

Boston

$246

Roundtrip

Found 1 hour ago

Select Frontier Airlines flight, departing Thu, Dec 10 from Chicago to Boston, returning Sat, Dec 12, priced at $246 Found 1 hour ago

Fri, Jan 22 - Mon, Feb 8

MDW

Chicago

BOS

Boston

$250

Roundtrip

Found 3 days ago

Select Frontier Airlines flight, departing Fri, Jan 22 from Chicago to Boston, returning Mon, Feb 8, priced at $250 Found 3 days ago

Tue, Oct 20 - Mon, Oct 26

MDW

Chicago

BOS

Boston

$258

Roundtrip

Found 4 days ago

Select Southwest Airlines flight, departing Tue, Oct 20 from Chicago to Boston, returning Mon, Oct 26, priced at $258 Found 4 days ago

Thu, Nov 12 - Sat, Nov 14

MDW

Chicago

BOS

Boston

$260

Roundtrip

Found 4 days ago

Select Southwest Airlines flight, departing Thu, Nov 12 from Chicago to Boston, returning Sat, Nov 14, priced at $260 Found 4 days ago

Sat, Nov 14 - Sun, Nov 15

MDW

Chicago

BOS

Boston

$261

Roundtrip

Found 5 days ago

Select Southwest Airlines flight, departing Sat, Nov 14 from Chicago to Boston, returning Sun, Nov 15, priced at $261 Found 5 days ago

Fri, Dec 4 - Sun, Dec 6

ORD

Chicago

BOS

Boston

$266

Roundtrip

Just found

Select Frontier Airlines flight, departing Fri, Dec 4 from Chicago to Boston, returning Sun, Dec 6, priced at $266 Just found

Mon, Oct 19 - Wed, Oct 21

ORD

Chicago

BOS

Boston

$276

Roundtrip

Just found

Select Delta flight, departing Mon, Oct 19 from Chicago to Boston, returning Wed, Oct 21, priced at $276 Just found

Sun, Oct 18 - Wed, Oct 21

ORD

Chicago

BOS

Boston

$281

Roundtrip

Just found

Select JetBlue Airways flight, departing Sun, Oct 18 from Chicago to Boston, returning Wed, Oct 21, priced at $281 Just found

Fri, Nov 6 - Sat, Nov 14

ORD

Chicago

BOS

Boston

$290

Roundtrip

Found 21 hours ago

Select United flight, departing Fri, Nov 6 from Chicago to Boston, returning Sat, Nov 14, priced at $290 Found 21 hours ago

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $281

BOS

Logan Intl.

CheapestClosest

7 min

Flights from $281

Find the cheapest month to fly from Chicago (CHI) to Boston (BOS)

November is typically the cheapest month to fly

From $179 - $402 per traveler.

Travel information

Origin airport	Chicago, IL
Destination airport	Logan International Airport
Distance	882 miles away
Roundtrip price	$246

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Flights

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Flights from Louisville (SDF) to Boston (BOS)
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Flights from Harrisburg (MDT) to Boston (BOS)
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Flights from London (LHR) to Boston (BOS)
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Flights from Jacksonville (JAX) to Boston (BOS)
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Flights from Grand Rapids (GRR) to Boston (BOS)
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Flights from Dallas (DFW) to Boston (BOS)
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Flights from Amsterdam (AMS) to Boston (BOS)
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Flights from Washington (IAD) to Boston (BOS)
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Flights from Portland (PDX) to Boston (BOS)
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Flights from Indianapolis (IND) to Boston (BOS)
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Flights from Berlin (BER) to Boston (BOS)
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Flights from São Paulo (GRU) to Boston (BOS)
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Flights from Orange County (SNA) to Boston (BOS)
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Flights from Fort Myers (RSW) to Boston (BOS)
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Flights from San Francisco (SFO) to Boston (BOS)
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Flights from White Plains (HPN) to Boston (BOS)
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Flights from Lisbon (LIS) to Boston (BOS)
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Flights from New York (NYC) to Boston (BOS)
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Flights from Athens (ATH) to Boston (BOS)
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Flights from Sacramento (SMF) to Boston (BOS)
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Flights from Delhi (DEL) to Boston (BOS)
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Flights from Tampa (TPA) to Boston (BOS)
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Flights from West Palm Beach (PBI) to Boston (BOS)
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Flights from Chicago (ORD) to Boston (BOS)
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Flights from New York (JFK) to Boston (BOS)
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Flights from Nashville (BNA) to Boston (BOS)
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Flights from Montego Bay (MBJ) to Boston (BOS)
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Flights from Honolulu (HNL) to Boston (BOS)
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Flights from San Jose (SJC) to Boston (BOS)
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Flights from Minneapolis (MSP) to Boston (BOS)
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Flights from Beijing (PEK) to Boston (BOS)
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Flights from Phoenix (PHX) to Boston (BOS)
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Flights from Seattle (SEA) to Boston (BOS)
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Flights from Asheville (AVL) to Boston (BOS)
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Flights from Des Moines (DSM) to Boston (BOS)
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Flights from Madison (MSN) to Boston (BOS)
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Flights from Milwaukee (MKE) to Boston (BOS)
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Flights from Birmingham (BHM) to Boston (BOS)
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Flights from Newark Liberty Intl. Airport (EWR) to Boston (BOS)
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Flights from Wilmington (ILM) to Boston (BOS)
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Flights from Atlanta (ATL) to Boston (BOS)
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Flights from Orlando (MCO) to Boston (BOS)
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Flights from St. Louis (STL) to Boston (BOS)
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Flights from Ontario Intl. Airport (ONT) to Boston (BOS)
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Flights from Pittsburgh (PIT) to Boston (BOS)
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Flights from Philadelphia (PHL) to Boston (BOS)
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Flights from Denver (DEN) to Boston (BOS)
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Flights from Knoxville (TYS) to Boston (BOS)
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Flights from Memphis (MEM) to Boston (BOS)
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Flights from Buffalo (BUF) to Boston (BOS)
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Flights from Houston (IAH) to Boston (BOS)
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Flights from Charleston (CHS) to Boston (BOS)
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Flights from Tokyo (NRT) to Boston (BOS)
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Flights from Greensboro (GSO) to Boston (BOS)
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Flights from Tucson (TUS) to Boston (BOS)
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Flights from San Antonio (SAT) to Boston (BOS)
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Flights from Fort Lauderdale (FLL) to Boston (BOS)
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Flights from Norfolk (ORF) to Boston (BOS)
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Flights from Bozeman (BZN) to Boston (BOS)
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Flights from Cincinnati (CVG) to Boston (BOS)
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Flights from Madrid (MAD) to Boston (BOS)
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Flights from Kansas City (MCI) to Boston (BOS)
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Flights from Cleveland (CLE) to Boston (BOS)
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Flights from Little Rock (LIT) to Boston (BOS)
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Flights from Myrtle Beach (MYR) to Boston (BOS)
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Flights from Toronto (YYZ) to Boston (BOS)
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Flights from Detroit (DTW) to Boston (BOS)
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$101 Cheap Flights from Chicago (CHI) to Boston (BOS)

Popular airlines from Chicago to Boston, MA (BOS-Logan Intl.)

Be in the know

Book smarter

Earn twice

Cheap Flights from Chicago to Boston (CHI-BOS)

Alternative airports near Boston

Find the cheapest month to fly from Chicago (CHI) to Boston (BOS)

November is typically the cheapest month to flyNovember is typically the cheapest month to fly

Travel information

Explore a world of travel with Expedia

November is typically the cheapest month to fly