Flights Boston-Chicago

Find cheap flights from Boston to Chicago in a few seconds with Jetcost

With a choice of airlines operating Boston to Chicago flights, planning your visit to this city is easy and once you've arrived you'll soon be enjoying its attractions whatever your age and interests. From world-class museums to beautiful beaches and theaters to soul food we guarantee you'll never be bored. While in Chicago be sure to:

  • Visit the Art Institute of Chicago and the Field Museum of Natural History
  • Learn all about animal conservation work at the Lincoln Park Zoo
  • Take the family to the Adler Planetarium and the Shedd Aquarium, with one of the best marine collections in America
  • Enjoy an architectural tour of the city and admire the buildings of Frank Lloyd Wright and Louis Sullivan
  • Take in the sweeping panoramic views from the top of the Sears Tower or the John Hancock Center
Chicago has an efficient and safe public transport network, the best way of seeing the Windy City sights, but for exploring further afield book a rental car at the same time as flights from Boston to Chicago. When you rent a car in Chicago you have the freedom and flexibility to get out into the forest parks that surround the city, sunbathe on Lake Michigan's beaches or head further afield to explore towns such as Madison or Milwaukee.

Your Boston to Chicago flights land at either O'Hare International or Midway airports. Whether you're renting a car or using the regular and efficient airport to city links you'll find a wide choice of hotels in Chicago within easy reach whatever your budget. So why not start searching for cheap flights from Boston to Chicago now?

Lowest round trip fares found for Boston to Chicago flights

Flight

Airline name

Price

Type

Trip dates

Search date

Boston - Chicago American Airlines $126 Round-trip 16 December 17 December
Boston - Chicago Southwest Airlines $139 Round-trip 27 December 02 January
Boston - Chicago American Airlines $142 Round-trip 16 December 20 December

Recent flight searches Boston - Chicago

Flight

Airline name

Price

Type

Trip dates

Search date

Provider

Boston - Chicago JetBlue $196 Round-trip 15 to 16 December Yesterday
Boston - Chicago JetBlue $98 One-way 24 May Yesterday
Boston - Chicago Southwest Airlines $169 Round-trip 02 to 04 January 2 days ago
Boston - Chicago Southwest Airlines $226 Round-trip 28 December to 02 January 2 days ago
Boston - Chicago American Airlines $177 Round-trip 16 to 19 December 2 days ago

Make the most of the short flying times and direct daily routes and book great deals on flights from Boston to Chicago now ready to take in the delights of the Windy City. With its picturesque and iconic skyline, Chicago lies on the shores of Lake Michigan and is a vibrant city full of music, culture, comedy, shopping, dining and family attractions.

Weather forecast for Chicago
  • Thursday 8
    Min 22 °F
    Max 27 °F
  • Friday 9
    Min 20 °F
    Max 25 °F
  • Saturday 10
    Min 22 °F
    Max 29 °F
  • Sunday 11
    Min 16 °F
    Max 32 °F
  • Monday 12
    Min 7 °F
    Max 27 °F
Climate in Chicago
  • Cold
     
     
     
     
    Hot
  •  
    Rain (mm)
    Days of rain
  • January
    29 °F
    17.00
    8
  • February
    32 °F
    25.00
    7
  • March
    41 °F
    39.00
    13
  • April
    51 °F
    57.00
    12
  • May
    60 °F
    108.00
    17
  • June
    69 °F
    87.00
    12
  • July
    75 °F
    94.00
    12
  • August
    73 °F
    98.00
    13
  • September
    68 °F
    59.00
    10
  • October
    55 °F
    66.00
    13
  • November
    44 °F
    61.00
    14
  • December
    32 °F
    31.00
    9