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Flights Boston — Chicago

Boston
BOS
Chicago
CHI

Cheap flights Boston — Chicago

Below you can see the best deals on flights Boston — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 11 August, from AED 283.

Top 10 cheap flights Boston — Chicago

Direct flights Boston — Chicago

Direct flight options for Boston — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by United Airlines — travel time is 2 h 44 min.

Top 10 direct flights Boston — Chicago

About the Boston — Chicago flight

On this page, you can find and buy flight tickets from Boston to Chicago. The flight distance is 1,369 km, and a high frequency of around 131 flights per week makes it easy to find a convenient departure time. Be sure to check the information on how to get to the airport before you leave.

Regular service is provided by American Airlines, United Airlines, and JetBlue. Ticket prices depend on the season and how far in advance you book, so we recommend using the price trends chart and studying ways of how to get from the airport after landing.

Return route:return route: flights Chicago → Boston

Flight schedule Boston — Chicago

The table shows direct flights Boston → Chicago on the selected date. The flight takes approximately 2 h 52 min. Regular flights are operated by American Airlines, United Airlines, Southwest Airlines and Delta. Departures from Logan International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time

Flight ticket prices by day: Boston — Chicago

Below is a calendar of the lowest flight ticket prices for Boston — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 263 in b, and the most expensive are around AED 414 in n. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Boston → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 428lowMayAED 443lowSepAED 418low
FebAED 428lowJunAED 579highOctAED 438low
MarAED 478mediumJulAED 604highNovAED 493medium
AprAED 478mediumAugAED 579highDecAED 594high

Some values are estimated based on seasonality.

When to fly

The warmest weather in Chicago occurs in July, when the average high reaches 26.5°C. January is the coldest month with temperatures as low as -5°C, while the peak precipitation and most humid weather are typically recorded in May.

The lowest ticket prices are observed in November, starting AED 263. Currently, the most expensive period to fly is February, with prices starting AED 405.

September is a great time to visit: the city enjoys comfortable temperatures around 23.5°C with moderate ticket costs. During the winter months, be sure to consider the risk of flight delays due to weather conditions.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Boston — Chicago ticket

  • We recommend planning your ticket purchase 4–6 weeks before departure to find deals AED 263.
  • Compare fares from Southwest (WN) and JetBlue (B6), as low-cost carriers often offer more favorable baggage terms on flights to Chicago.
  • Use the low-price calendar on this page: mid-week departures (Tuesday or Wednesday) are usually cheaper than weekend flights.
  • Pay attention to the arrival airport, as choosing between O'Hare and Midway can affect the final cost of your transfer to the city center.

Airlines

Major carriers such as United Airlines, American Airlines, and JetBlue operate on the Boston–Chicago route, providing the bulk of the 131 weekly flights. Most flights are non-stop, making this a convenient route for both business and leisure travel. Detailed information on departure times and route options can be found in the list of airlines below.

  • American Airlines
    American AirlinesAA
    45x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight BOS → ORD45x/week
      Duration
      3h 6m
      Days
      un,MonS
    34.0%Open →
  • United Airlines
    United AirlinesUA
    41x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight BOS → ORD41x/week
      Duration
      2h 55m
      Days
      un,MonS
    31.0%Open →
  • Southwest Airlines
    Southwest AirlinesWN
    13x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight BOS → MDW13x/week
      Duration
      2h 43m
      Days
      un,MonS
    9.6%Open →
  • Delta
    DeltaDL
    12x/week
    WebsiteFleet: 986190M pax/year
    • Direct flight BOS → ORD12x/week
      Duration
      2h 59m
      Days
      un,MonS
    9.4%Open →
  • JetBlue
    JetBlueB6
    9x/week
    WebsiteFleet: 30742.5M pax/year
    • Direct flight BOS → ORD9x/week
      Duration
      3h
      Days
      un,MonS
    6.6%Open →
  • Japan Airlines
    Japan AirlinesJL
    3x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight BOS → ORD3x/week
    2.5%Open →
  • Iberia
    IberiaIB
    3x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight BOS → ORD3x/week
    2.3%Open →
  • British Airways
    British AirwaysBA
    3x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight BOS → ORD3x/week
    2.0%Open →
  • Alaska Airlines
    Alaska AirlinesAS
    2x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight BOS → ORD2x/week
      Duration
      3h
      Days
      un,MonS
    1.3%Open →
  • Virgin Atlantic
    Virgin AtlanticVS
    1x/week
    WebsiteFleet: 415.3M pax/year
    • Direct flight BOS → ORD1x/week
    0.5%Open →
  • SAS
    SASSK
    1x/week
    WebsiteFleet: 13524M pax/year
    • Direct flight BOS → ORD1x/week
    0.3%Open →
  • Latam Airlines Group
    Latam Airlines GroupLA
    1x/week
    WebsiteFleet: 34782M pax/year
    • Direct flight BOS → ORD1x/week
    0.3%Open →

Cities and airports on the Boston — Chicago route

Flights Boston — Chicago depart from Logan International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Boston

BOS
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Boston — Chicago flight

How long is the flight from Boston to Chicago?

The distance between the cities is 1,369 km. A direct flight usually takes about 2 hours and 10 minutes, depending on the airline and weather conditions.

Which airlines fly from Boston to Chicago?

United Airlines, American Airlines, JetBlue, Southwest, and several other American and international carriers operate on this route.

Are there direct flights?

Yes, there are many direct flights between the cities every day, allowing you to choose a convenient departure time in the morning, afternoon, or evening.

How much is the cheapest ticket?

Flight prices constantly change based on demand. You can see the current minimum for specific dates in the low-price calendar on this page.

Which airport does the flight arrive at?

Flights from Boston arrive at the main Chicago airports. Detailed information about the arrival terminal can be found in the details of your selected ticket.

Where else you can fly from Boston

New York City
New York City∙18 July
AED 303
Washington, D.C.
Washington, D.C.∙8 July
AED 464

Where else you can fly to Chicago from

New York City
New York City∙14 July
AED 341
Toronto
Toronto∙13 July
AED 514
Washington, D.C.
Washington, D.C.∙15 July
AED 364
Detroit
Detroit∙14 July
AED 266
Minneapolis
Minneapolis∙22 July
AED 220
Atlanta
Atlanta∙30 June
AED 226
Los Angeles
Los Angeles∙21 July
AED 420
Montreal
Montreal∙8 July
AED 700
London
London∙6 July
AED 1,999
Mexico City
Mexico City∙4 July
AED 766
Cancun
Cancun∙1 July
AED 723
Guadalajara
Guadalajara∙17 July
AED 856