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Boston Logan International Airport to Chicago flight

Explore the cheapest one-way and round-trip flights from Boston Logan International Airport to Chicago over the next 90 days, with one-way fares from €76 and round-trip from €136. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        BOS 07:30
        2h 54m
        Nonstop
        ORD 09:24
        Boston - Chicago | Mon, Oct 12 | Delta Air Lines
        ORD 07:35
        2h 33m
        Nonstop
        BOS 11:08
        Chicago - Boston | Mon, Oct 19 | Delta Air Lines
        €144 €359
        60% off
        60% off
        €359 €144
      • BOS 16:30
        2h 58m
        Nonstop
        ORD 18:28
        Boston - Chicago | Fri, Oct 9 | Delta Air Lines
        ORD 07:35
        2h 33m
        Nonstop
        BOS 11:08
        Chicago - Boston | Sat, Oct 10 | Delta Air Lines
        €149 €359
        57% off
        57% off
        €359 €149
      • BOS 05:54
        3h 6m
        Nonstop
        ORD 08:00
        Boston - Chicago | Sun, Nov 8 | American Airlines
        ORD 19:03
        2h 34m
        Nonstop
        BOS 22:37
        Chicago - Boston | Tue, Nov 10 | American Airlines
        €152 €359
        57% off
        57% off
        €359 €152
      • BOS 17:00
        3h 12m
        Nonstop
        ORD 19:12
        Boston - Chicago | Wed, Nov 25 | Jetblue Airways
        MDW 08:30
        2h 30m
        Nonstop
        BOS 12:00
        Chicago - Boston | Sun, Nov 29 |
        €152
        57% off
        €359 €152
      • BOS 07:00
        3h 6m
        Nonstop
        ORD 09:06
        Boston - Chicago | Mon, Oct 12 | American Airlines
        ORD 20:10
        2h 35m
        Nonstop
        BOS 23:45
        Chicago - Boston | Mon, Oct 19 | American Airlines
        €153
        56% off
        €359 €153
      • BOS 12:31
        3h 9m
        Nonstop
        ORD 14:40
        Boston - Chicago | Sat, Nov 21 | American Airlines
        ORD 06:59
        2h 29m
        Nonstop
        BOS 10:28
        Chicago - Boston | Wed, Nov 25 | American Airlines
        €153
        56% off
        €359 €153
      • BOS 13:34
        3h 1m
        Nonstop
        ORD 15:35
        Boston - Chicago | Wed, Oct 14 | American Airlines
        ORD 06:50
        2h 39m
        Nonstop
        BOS 10:29
        Chicago - Boston | Wed, Oct 21 | American Airlines
        €264
        26% off
        €359 €264
      • BOS 18:00
        2h 59m
        Nonstop
        ORD 19:59
        Boston - Chicago | Wed, Oct 14 | Delta Air Lines
        ORD 16:35
        2h 45m
        Nonstop
        BOS 20:20
        Chicago - Boston | Wed, Oct 21 | Delta Air Lines
        €269
        25% off
        €359 €269
      • BOS 12:54
        6h 29m
        1 stop
        ORD 18:23
        Boston - Chicago | Wed, Oct 14 | Frontier Airlines
        ORD 11:30
        2h 45m
        Nonstop
        BOS 15:15
        Chicago - Boston | Wed, Oct 21 | Delta Air Lines
        €136
        62% off
        €359 €136
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Oct 10 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        BOS 16:00
        Chicago - Boston | Mon, Oct 12 | Normal Airline
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      • Cheapest nonstop
        BOS 05:54
        3h 6m
        Nonstop
        ORD 08:00
        Boston - Chicago | Sat, Oct 31 | American Airlines
        €85 €114
        25% off
        25% off
        €114 €85
      • BOS 13:33
        3h 4m
        Nonstop
        ORD 15:37
        Boston - Chicago | Sat, Nov 7 | American Airlines
        €85 €114
        25% off
        25% off
        €114 €85
      • BOS 13:35
        2h 52m
        Nonstop
        ORD 15:27
        Boston - Chicago | Sat, Nov 21 | Delta Air Lines
        €85 €114
        25% off
        25% off
        €114 €85
      • BOS 07:30
        2h 54m
        Nonstop
        ORD 09:24
        Boston - Chicago | Sun, Nov 22 | Delta Air Lines
        €85
        25% off
        €114 €85
      • BOS 07:14
        3h 16m
        Nonstop
        ORD 09:30
        Boston - Chicago | Sun, Nov 22 | American Airlines
        €85
        25% off
        €114 €85
      • BOS 19:40
        2h 51m
        Nonstop
        ORD 21:31
        Boston - Chicago | Sun, Nov 15 | Delta Air Lines
        €85
        25% off
        €114 €85
      • BOS 19:40
        2h 51m
        Nonstop
        ORD 21:31
        Boston - Chicago | Sat, Nov 7 | Delta Air Lines
        €85
        25% off
        €114 €85
      • BOS 07:00
        3h 5m
        Nonstop
        ORD 09:05
        Boston - Chicago | Sun, Nov 15 | American Airlines
        €85
        25% off
        €114 €85
      • BOS 07:30
        2h 54m
        Nonstop
        ORD 09:24
        Boston - Chicago | Thu, Nov 19 | Delta Air Lines
        €85
        25% off
        €114 €85
      • BOS 19:40
        3h 14m
        Nonstop
        ORD 21:54
        Boston - Chicago | Sat, Nov 21 | American Airlines
        €85
        25% off
        €114 €85
      • BOS 06:55
        2h 52m
        Nonstop
        ORD 08:47
        Boston - Chicago | Sat, Oct 31 | Jetblue Airways
        €85
        25% off
        €114 €85
      • BOS 12:15
        7h 1m
        1 stop
        ORD 18:16
        Boston - Chicago | Sat, Nov 21 | Frontier Airlines
        €76
        33% off
        €114 €76
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Oct 10 | Normal Airline
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Displayed flight fares from Boston Logan International Airport to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Trip.com Price Insights: Flights from Boston Logan International Airport to Chicago

What is the cheapest month for one-way flights from Boston Logan International Airport to Chicago?

Data is based on average one-way flight prices from Boston Logan International Airport to Chicago in Trip.com's database over the past 12 months.

According to Trip.com's data from the past 12 months, the cheapest month for one-way flights from Boston Logan International Airport to Chicago is January, with an average price of €114. In contrast, the most expensive month is usually October, with an average price of €183.

€183
€149
€114
€80
    Cheapest
  • €183
    Oct
  • €153
    Nov
  • €116
    Dec
  • €114
    Jan
  • €141
    Feb
  • €143
    Mar
  • €136
    Apr
  • €120
    May
  • €122
    Jun
  • €135
    Jul
  • €130
    Aug
  • €141
    Sep

What is the cheapest day of the week to fly from Boston Logan International Airport to Chicago?

The data is based on the past 12 months and shows the average ticket prices from Boston Logan International Airport to Chicago for each day of the week in the Trip.com database.

Based on Trip.com’s data from the past 12 months, the cheapest day to depart from Boston Logan International Airport to Chicago is Tuesday, with average fares usually lower than on other days. Avoid flying on Sunday, as ticket prices are typically highest that day.

€172
€144
€116
€88
  • €131
    Mon
  • €116
    Tue
  • €127
    Wed
  • €143
    Thu
  • €141
    Fri
  • €131
    Sat
  • €172
    Sun

Which airlines are the most popular for Boston Logan International Airport to Chicago flights?

See which airlines fly from Boston Logan International Airport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.
United Airlines logo United Airlines

Flight Schedule from Boston Logan International Airport to Chicago

Check the schedule for flights from Boston Logan International Airport to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2804

    Boston Logan International Airport

    20:10

    BOS

    2h 54m

    22:04

    ORD

    S M T W T F S
    Search

  2. DL2570

    Boston Logan International Airport

    07:30

    BOS

    2h 54m

    09:24

    ORD

    S M T W T - S
    Search

  3. AA927

    Boston Logan International Airport

    19:23

    BOS

    3h 6m

    21:29

    ORD

    S M T W T F S
    Search

  4. B6811

    Boston Logan International Airport

    17:10

    BOS

    3h 5m

    19:15

    ORD

    S M T W T F S
    Search

  5. AA1239

    Boston Logan International Airport

    08:12

    BOS

    3h 18m

    10:30

    ORD

    S M T W T F S
    Search

  6. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Nonstop

    16:04

    ATL

    S M T W T F S
    Search

  7. F91595

    Hartsfield–Jackson Atlanta International Airport

    17:02

    ATL

    2h 21m

    Nonstop

    18:23

    ORD

    S M T W T F S

  8. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Nonstop

    16:04

    ATL

    S M T W T F S
    Search

  9. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:55

    ATL

    1h 56m

    Nonstop

    17:51

    MDW

    - - - W - - S

  10. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Nonstop

    16:04

    ATL

    S M T W T F S
    Search

  11. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 53m

    Nonstop

    23:43

    MDW

    S M T W T F S
Find more flights and airlines

What to know about flights from Boston Logan International Airport to Chicago?

Cheapest return ticket price €152
Cheapest one-way flight price €55
Off-season for travel August
Peak season for travel January

FAQs for Boston Logan International Airport to Chicago Flights

  • When is peak season for travel to Chicago?

    ؜The peak travel time for visiting Chicago is October. During this time, flights from Boston Logan International Airport to Chicago are the most expensive. Cheap tickets can still be booked on Trip.com.
  • Flights from Boston Logan International Airport (BOS) to O'Hare International Airport (CHI) take around 3 hours.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 05:15 and arrives in Chicago (ORD) at 07:15.
  • The latest flight departs from Boston Logan International Airport (BOS) at 20:51 and arrives in Chicago (ORD) at 22:52.
    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
  • Yes. United Airlines and American Airlines operate direct flights from Boston Logan International Airport to Chicago. The average flight time is approximately 2 hours 13 minutes, with about 21 flights per week. Actual schedules may vary by season.
  • The cheapest one-way flight from Boston Logan International Airport to Chicago currently starts from €76, with round-trip fares from €136. The lowest fare is offered by Frontier Airlines departing on Sat, Nov 21; prices are subject to availability.
  • Yes. The average flight time from Boston Logan International Airport to Chicago is about 2 hours 15 minutes. Actual flight time may vary due to routing, weather, and air traffic.
  • Currently, multiple airlines offer flights from Boston Logan International Airport to Chicago, including: American Airlines Delta Air Lines Jetblue Airways United Airlines The selected airlines are based on Trip.com user booking data from the past 90 days.
  • Based on Trip.com flight data for departures within the next 30 days, the average one-way fare from Boston Logan International Airport to Chicago is €232, and the average round-trip fare is €430. Prices may vary depending on the departure date, airline, and availability.
  • Flights from Boston Logan International Airport to Chicago are usually cheapest in January, with an average one-way fare of about €232. Prices may vary depending on the departure date, airline, and availability.
  • The earliest flight from Boston Logan International Airport to Chicago departs at 05:50, and the latest one departs at 22:00. There are approximately 32 flights per day. Flight times may change, so please check the latest departure and arrival times before your trip.
  • Flights from Boston Logan International Airport to Chicago usually arrive at Chicago Midway International Airport and O'Hare International Airport. O'Hare International Airport is the most convenient option for this route.
  • Jetblue Airwaysand WestJet are the most popular budget airlines flying from Boston Logan International Airport to Chicago. Basic fares start from €76. Before comparing final prices, watch out for baggage, seat selection, and payment surcharges.

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