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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 fares from Boston Logan International Airport to Chicago Midway International Airport are based on average airline prices for the next 3 months, according to 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 AED 407
Hahn Air
From AED 449
Delta Air Lines
From AED 530

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 does it take to fly 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 AED 649 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 AED 846 in July, the most expensive month to book this route.
    • 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.

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

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Prices displayed on this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within the last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

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Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.