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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 $202 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Sat, Dec 5 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$202

Roundtrip

Just found

Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Boston, returning Mon, Dec 7, priced at $202 Just found

Sat, Dec 5 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$211

Roundtrip

Just found

Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Boston, returning Mon, Dec 7, priced at $211 Just found

Sat, Dec 5 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$217

Roundtrip

Just found

Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Boston, returning Mon, Dec 7, priced at $217 Just found

Sat, Dec 5 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$217

Roundtrip

Just found

Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Boston, returning Mon, Dec 7, priced at $217 Just found

Sat, Dec 5 - Mon, Dec 7

MDW

Chicago

BOS

Boston

$219

Roundtrip

Just found

Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Boston, returning Mon, Dec 7, priced at $219 Just found

Mon, Nov 9 - Wed, Nov 11

MDW

Chicago

BOS

Boston

$221

Roundtrip

Just found

Select Southwest Airlines flight, departing Mon, Nov 9 from Chicago to Boston, returning Wed, Nov 11, priced at $221 Just found

Thu, Dec 10 - Mon, Dec 14

ORD

Chicago

BOS

Boston

$246

Roundtrip

Found 1 hour ago

Select Frontier Airlines flight, departing Thu, Dec 10 from Chicago to Boston, returning Mon, Dec 14, priced at $246 Found 1 hour ago

Wed, Oct 21 - Tue, Oct 27

ORD

Chicago

BOS

Boston

$315

Roundtrip

Just found

Select Delta flight, departing Wed, Oct 21 from Chicago to Boston, returning Tue, Oct 27, priced at $315 Just found

Wed, Oct 21 - Tue, Oct 27

ORD

Chicago

BOS

Boston

$315

Roundtrip

Just found

Select American Airlines flight, departing Wed, Oct 21 from Chicago to Boston, returning Tue, Oct 27, priced at $315 Just found

Wed, Oct 21 - Tue, Oct 27

ORD

Chicago

BOS

Boston

$315

Roundtrip

Just found

Select United flight, departing Wed, Oct 21 from Chicago to Boston, returning Tue, Oct 27, priced at $315 Just found

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 $276

BOS

Logan Intl.

CheapestClosest

7 min

Flights from $276

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 O'Hare Intl. Airport
Destination airport	Logan International Airport
Distance	863 miles away
Airlines serving	JetBlue Airways, American Airlines, Delta, United, Alaska Airlines, Frontier Airlines, Sun Country Airlines
Popular airline	JetBlue Airways
Roundtrip price	$202
Average flight time	2 hours 38 mins

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Flights

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Flights from San Diego (SAN) to Boston (BOS)
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Flights from Baltimore (BWI) to Boston (BOS)
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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 New Orleans (MSY) to Boston (BOS)
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Flights from Washington (DCA) 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 Santo Domingo (SDQ) to Boston (BOS)
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Flights from Milwaukee (MKE) to Boston (BOS)
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Flights from Tel Aviv (TLV) to Boston (BOS)
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Flights from Barcelona (BCN) to Boston (BOS)
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Flights from Salt Lake City (SLC) 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 Pittsburgh (PIT) to Boston (BOS)
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Flights from Philadelphia (PHL) to Boston (BOS)
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Flights from Buffalo (BUF) 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