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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 09:05
        4h 37m
        1 stop
        MDW 12:42
        Boston - Chicago | Wed, May 27 | Delta Air Lines
        ORD 18:06
        6h 22m
        1 stop
        BOS 01:28
        Chicago - Boston | Mon, Jun 1 | Delta Air Lines
        € 118 € 153
        23% off
        23% off
        € 153 € 118
      • BOS 05:51
        8h 28m
        1 stop
        MDW 13:19
        Boston - Chicago | Sat, May 30 | Delta Air Lines
        MDW 18:36
        3h 53m
        1 stop
        BOS 23:29
        Chicago - Boston | Mon, Jun 1 | Delta Air Lines
        € 118 € 153
        23% off
        23% off
        € 153 € 118
      • BOS 05:40
        4h 3m
        1 stop
        MDW 08:43
        Boston - Chicago | Wed, May 13 | Delta Air Lines
        ORD 07:05
        6h 10m
        1 stop
        BOS 14:15
        Chicago - Boston | Wed, May 20 | Delta Air Lines
        € 120 € 153
        22% off
        22% off
        € 153 € 120
      • BOS 05:51
        8h 28m
        1 stop
        MDW 13:19
        Boston - Chicago | Mon, Jun 1 | Delta Air Lines
        ORD 07:05
        5h 15m
        1 stop
        BOS 13:20
        Chicago - Boston | Tue, Jun 2 | Delta Air Lines
        € 124
        19% off
        € 153 € 124
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, May 11 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Wed, May 13 | Normal Airline
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      • Cheapest nonstop
        BOS 10:45
        2h 40m
        Direct
        MDW 12:25
        Boston - Chicago | Tue, Jun 9 | Hahn Air
        € 55 € 90
        39% off
        39% off
        € 90 € 55
      • BOS 18:20
        2h 50m
        Direct
        MDW 20:10
        Boston - Chicago | Tue, Jun 2 | Hahn Air
        € 55 € 90
        39% off
        39% off
        € 90 € 55
      • BOS 14:25
        2h 40m
        Direct
        MDW 16:05
        Boston - Chicago | Tue, May 12 | Hahn Air
        € 65 € 90
        28% off
        28% off
        € 90 € 65
      • BOS 17:30
        2h 50m
        Direct
        MDW 19:20
        Boston - Chicago | Mon, Jul 6 | Hahn Air
        € 68
        24% off
        € 90 € 68
      • BOS 15:45
        2h 45m
        Direct
        MDW 17:30
        Boston - Chicago | Wed, May 27 | Hahn Air
        € 72
        20% off
        € 90 € 72
      • BOS 05:30
        4h 44m
        1 stop
        MDW 09:14
        Boston - Chicago | Mon, Jun 29 | Delta Air Lines
        € 68
        24% off
        € 90 € 68
      • BOS 05:40
        10h 15m
        1 stop
        MDW 14:55
        Boston - Chicago | Sun, Jun 7 | Hahn Air
        € 72
        20% off
        € 90 € 72
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, May 11 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

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 € 79
Delta Air Lines
From € 124
Hahn Air
From € 139

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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. F93085

    Boston Logan International Airport

    06:00

    BOS

    3h 8m

    Direct

    09:08

    ATL

    S M T W T F S
    Search

  2. F92779

    Hartsfield-Jackson Atlanta International Airport

    21:22

    ATL

    2h 4m

    Direct

    22:26

    MDW

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

Flight distance1,380.83km
Cheapest one-way ticket price€ 55
Cheapest return ticket price€ 118

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 43 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 € 208 in June, 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 € 319 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 Chicago 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 Chicago O'Hare International Airport. The distance is around 25km.

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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

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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.