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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 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Tue, Jul 14 | Normal Airline
        Search
        Search
      • BOS 3:10 PM
        7h 36m
        1 stop
        MDW 9:46 PM
        Boston - Chicago | Wed, Sep 2 | Delta Air Lines
        €62 €100
        38% off
        38% off
        €100 €62
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Boston - Chicago | Sun, Jul 12 | Normal Airline
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Displayed flight fares from Boston Logan International Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

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.

Delta Air Lines
From €62
Frontier Airlines
From €99
Hahn Air
From €128

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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

    5:30 AM

    BOS

    2h 24m

    Nonstop

    7:54 AM

    DTW

    S M T W T F S
    Search

  2. DL4684

    Detroit Metropolitan Wayne County Airport

    8:55 AM

    DTW

    1h 23m

    Nonstop

    9:18 AM

    MDW

    S M T W T F S
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Boston Logan International Airport to Chicago Midway International Airport Flights Info

Flight distance 1,380.83 km
Cheapest one-way ticket price €62

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

  • How long is a flight from Boston Logan International Airport to Chicago Midway International Airport?

    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 06:20 and arrives in Chicago Midway International Airport (MDW) at 08:15.
  • The latest flight departs from Boston Logan International Airport (BOS) at 20:05 and arrives in Chicago Midway International Airport (MDW) at 21:55.
    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.

Popular Destinations

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 in 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, WLAN, 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 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.