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Boston Logan International Airport to Chicago Midway International Airport flight

Search for flights from Boston to Chicago and check out affordable one-way and round-trip options.

      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        Search
        Search

Flight prices from Boston Logan International Airport to Chicago Midway International Airport are based on the average fares across airlines for the next three months, based on Trip.com’s latest data.

Selected Airlines from Boston Logan International Airport to Chicago Midway International Airport

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

Frontier Airlines
From € 97
Hahn Air
From € 107
Delta Air Lines
From € 126

Find more flights and airlines

Flight Schedule from Boston Logan International Airport to Chicago Midway International Airport

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

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1019

    Boston Logan International Airport

    05:30

    BOS

    2h 24m

    Direct

    07:54

    DTW

    S M T W T F S
    Search

  2. DL4684

    Detroit Metropolitan Wayne County Airport

    08:55

    DTW

    1h 23m

    Direct

    09:18

    MDW

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

Boston Logan International Airport to Chicago Midway International Airport Flights Info

Flight distance 1,380.83km

FAQs for Boston Logan International Airport to Chicago Midway International Airport Flights

  • How long is a flight from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW)?

    It takes around 2 hours 44 minutes to fly from Boston Logan International Airport (bos) to Chicago Midway International Airport (mdw).
  • There are around 5 daily flights from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW).
  • Tickets cost around € 155 in September, making it the cheapest month to book. Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.
  • The route from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around € 202 in July, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 05:10 and arrives in Chicago Midway International Airport (MDW) at 07:00.
  • The latest flight departs from Boston Logan International Airport (BOS) at 21:40 and arrives in Chicago Midway International Airport (MDW) at 23:25.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.

Popular Destinations & Recommendations

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.