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Boston Logan International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Boston Logan International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from HK$665 and round-trip from HK$1,493. Based on Trip.com's latest 7-day flight data.

      • BOS 09:15
        4h 32m
        1 stop
        MDW 12:47
        Boston - Chicago | Wed, Oct 7 | Delta Air Lines
        ORD 16:40
        2h 41m
        Nonstop
        BOS 20:21
        Chicago - Boston | Sun, Oct 11 | Delta Air Lines
        HK$1,493 HK$3,058
        51% off
        51% off
        HK$3,058 HK$1,493
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, Oct 5 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        BOS 16:00
        Chicago - Boston | Wed, Oct 7 | Normal Airline
        More cheap flights
        More cheap flights
      • Cheapest nonstop
        BOS 17:50
        2h 45m
        Nonstop
        MDW 19:35
        Boston - Chicago | Wed, Nov 18 | Hahn Air
        HK$828 HK$1,312
        37% off
        37% off
        HK$1,312 HK$828
      • BOS 16:20
        2h 35m
        Nonstop
        MDW 17:55
        Boston - Chicago | Thu, Oct 15 | Hahn Air
        HK$861 HK$1,312
        34% off
        34% off
        HK$1,312 HK$861
      • BOS 12:15
        6h 32m
        1 stop
        MDW 17:47
        Boston - Chicago | Wed, Nov 4 | Frontier Airlines
        HK$665 HK$1,312
        49% off
        49% off
        HK$1,312 HK$665
      • BOS 11:12
        7h 15m
        1 stop
        MDW 17:27
        Boston - Chicago | Wed, Oct 28 | Frontier Airlines
        HK$918
        30% off
        HK$1,312 HK$918
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, Oct 5 | Normal Airline
        More cheap flights
        More cheap flights

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.

Which airline offers the cheapest flights from Boston Logan International Airport to Chicago Midway International Airport?

The cheapest airline flying from Boston Logan International Airport to Chicago Midway International Airport is Frontier Airlines (from HK$665) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From HK$665
Hahn Air
From HK$828
Delta Air Lines
From HK$1,116

Find more flights and airlines

What is the flight schedule from Boston Logan International Airport to Chicago Midway International Airport?

Check on the flight schedule from Boston to Chicago to find the flight that matches your travel plan.

Flight info.
Departure
Arrival
Weekly Schedule

  1. F93511

    Boston Logan International Airport

    12:54

    BOS

    3h 6m

    Nonstop

    16:00

    ATL

    S M T W T F S
    Search

  2. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:55

    ATL

    1h 56m

    Nonstop

    17:51

    MDW

    S M T W - - S

  3. DL2222

    Boston Logan International Airport

    12:55

    BOS

    2h 18m

    Nonstop

    15:13

    DTW

    S M T W T F S
    Search

  4. DL4677

    Detroit Metropolitan Wayne County Airport

    18:15

    DTW

    1h 22m

    Nonstop

    18:37

    MDW

    S M T W T F S

  5. DL923

    Boston Logan International Airport

    08:00

    BOS

    3h 6m

    Nonstop

    11:06

    ATL

    S M T W T F S
    Search

  6. DL1728

    Hartsfield–Jackson Atlanta International Airport

    15:30

    ATL

    1h 55m

    Nonstop

    16:25

    MDW

    S M T W T F S

  7. F93511

    Boston Logan International Airport

    12:54

    BOS

    3h 6m

    Nonstop

    16:00

    ATL

    S M T W T F S
    Search

  8. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 54m

    Nonstop

    23:44

    MDW

    S - - W T F S
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About Boston Logan International Airport and Chicago Midway International Airport

Learn about Boston Logan International Airport (BOS) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 1,380.83 km
Cheapest one-way ticket price HK$665
Cheapest return ticket price HK$1,493

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

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

    Boston Logan International Airport to Chicago Midway International Airport takes about 2 hours 28 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 5 daily flights from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW).
  • The earliest flight from Boston Logan International Airport to Chicago Midway International Airport departs at 05:50, and the last departs at 22:00, with about 19 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • 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 HK$1,787 in October, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport at 08:50 and arrives in Chicago Midway International Airport at 10:40.
  • The latest flight departs from Boston Logan International Airport at 20:50 and arrives in Chicago Midway International Airport at 22:35.
    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • One-way flights from Boston Logan International Airport to Chicago Midway International Airport currently start from HK$665, and round-trip fares start from HK$1,493. The current lowest fare is a Frontier Airlines flight departing on Wed, Nov 4; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Boston Logan International Airport to Chicago Midway International Airport is HK$1,411. Prices may vary depending on the departure date, airline, and availability.
  • Enter Boston Logan International Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

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Note: Prices shown on this page are the estimated lowest 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 clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date 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.