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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 | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Mon, Jul 13 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Sat, Jul 11 | Normal Airline
        Search
        Search

Flight fares 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 MYR 463
Hahn Air
From MYR 584
Delta Air Lines
From MYR 599

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 the flights 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 MYR 721 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 MYR 939 in July, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 05:20 and arrives in Chicago Midway International Airport (MDW) at 06:55.
  • The latest flight departs from Boston Logan International Airport (BOS) at 18:35 and arrives in Chicago Midway International Airport (MDW) at 20:20.
    • 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.

Most popular destination

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, regulatory fees, etc) with all fees confirmed before payment. Fees for baggage, 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 last 24 hours—even in real-time. The more popular the route, the more precise the data.

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