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 United Airlines $96 Round-trip 28 February 07 March
Boston - Chicago Spirit Airlines $108 Round-trip 16 August 23 August
Boston - Chicago Spirit Airlines $110 Round-trip 15 August 19 August

Recent flight searches Boston - Chicago

Flight

Airline name

Price

Type

Trip dates

Search date

Provider

Boston - Chicago Delta Airlines $222 Round-trip 04 to 10 March Today 15:01
Boston - Chicago JetBlue $154 Round-trip 03 to 07 March Today 14:57
Boston - Chicago American Airlines $141 One-way 21 February Today 07:58
Boston - Chicago Spirit Airlines $108 Round-trip 16 to 23 August Today 06:26
Boston - Chicago Delta Airlines $193 Round-trip 26 February to 05 March Today 00:07

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
  • Sunday 19
    Min 33 °F
    Max 55 °F
  • Monday 20
    Min 55 °F
    Max 62 °F
  • Tuesday 21
    Min 46 °F
    Max 59 °F
  • Wednesday 22
    Min 48 °F
    Max 62 °F
  • Thursday 23
    Min 42 °F
    Max 57 °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