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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 QAR 321 and round-trip from QAR 656. Based on Trip.com's latest 7-day flight data.

    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      ORD 05:40
      27h 31m
      1 stop
      BOS 10:11
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      QAR 656 QAR 786
      17% off
      17% off
      QAR 786 QAR 656
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      QAR 663 QAR 786
      16% off
      16% off
      QAR 786 QAR 663
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Wed, Nov 18 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      QAR 663 QAR 786
      16% off
      16% off
      QAR 786 QAR 663
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Sat, Nov 21 | Frontier Airlines
      QAR 663
      16% off
      QAR 786 QAR 663
    • BOS 10:25
      10h 5m
      1 stop
      MDW 19:30
      Boston - Chicago | Thu, Dec 17 | Frontier Airlines
      MDW 20:35
      11h 55m
      1 stop
      BOS 09:30
      Chicago - Boston | Sat, Dec 19 | Frontier Airlines
      QAR 667
      15% off
      QAR 786 QAR 667
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
      CHI 15:00
      6h
      Direct
      BOS 16:00
      Chicago - Boston | Thu, Oct 29 | Normal Airline
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    • Cheapest
      BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      QAR 321 QAR 440
      27% off
      27% off
      QAR 440 QAR 321
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Nov 14 | Frontier Airlines
      QAR 322 QAR 440
      27% off
      27% off
      QAR 440 QAR 322
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      QAR 343 QAR 440
      22% off
      22% off
      QAR 440 QAR 343
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      QAR 359
      18% off
      QAR 440 QAR 359
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      QAR 379
      14% off
      QAR 440 QAR 379
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      QAR 601 QAR 742
      19% off
      19% off
      QAR 742 QAR 601
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      QAR 601 QAR 742
      19% off
      19% off
      QAR 742 QAR 601
    • BOS 05:30
      4h 20m
      1 stop
      MDW 08:50
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      QAR 605 QAR 742
      18% off
      18% off
      QAR 742 QAR 605
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      QAR 639
      14% off
      QAR 742 QAR 639
    • BOS 05:30
      5h 16m
      1 stop
      MDW 09:46
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      QAR 660
      11% off
      QAR 742 QAR 660
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      QAR 379 QAR 440
      14% off
      14% off
      QAR 440 QAR 379
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      QAR 359 QAR 440
      18% off
      18% off
      QAR 440 QAR 359
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Nov 14 | Frontier Airlines
      QAR 322 QAR 440
      27% off
      27% off
      QAR 440 QAR 322
    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      QAR 321
      27% off
      QAR 440 QAR 321
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      QAR 343
      22% off
      QAR 440 QAR 343
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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Displayed flight fares from Boston to Chicago 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 QAR 321) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From QAR 321
Delta Air Lines
From QAR 379
Hahn Air
From QAR 531

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What is the 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. DL1748

    Boston Logan International Airport

    09:00

    BOS

    2h 26m

    Direct

    11:26

    DTW

    S M T W T F S
    Search

  2. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Direct

    12:47

    MDW

    S M T W T F S

  3. DL1103

    Boston Logan International Airport

    11:29

    BOS

    3h 26m

    Direct

    13:55

    MSP

    S M T W T F S
    Search

  4. DL4714

    Minneapolis-Saint Paul International Airport

    15:08

    MSP

    1h 39m

    Direct

    16:47

    MDW

    S M T W T F S

  5. DL2222

    Boston Logan International Airport

    12:55

    BOS

    2h 18m

    Direct

    15:13

    DTW

    S M T W T F S
    Search

  6. DL4677

    Detroit Metropolitan Wayne County Airport

    17:40

    DTW

    1h 20m

    Direct

    18:00

    MDW

    S M T W T F S

  7. DL2464

    Boston Logan International Airport

    18:55

    BOS

    3h 5m

    Direct

    22:00

    ATL

    S M T - - - -
    Search

  8. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  9. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Direct

    16:04

    ATL

    S M T W T F S
    Search

  10. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    - M T W T F S

  11. DL1710

    Boston Logan International Airport

    15:10

    BOS

    3h 1m

    Direct

    18:11

    ATL

    S M T W T F S
    Search

  12. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  13. DL2330

    Boston Logan International Airport

    16:20

    BOS

    3h 3m

    Direct

    19:23

    ATL

    S M T W T F S
    Search

  14. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  15. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Direct

    16:04

    ATL

    S M T W T F S
    Search

  16. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - 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 1,380.83km
Cheapest one-way ticket price QAR 321
Cheapest return ticket price QAR 656

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 15 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 3 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 22:50, with about 12 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 QAR 948 in November, 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.
  • One-way flights from Boston Logan International Airport to Chicago Midway International Airport currently start from QAR 321, and round-trip fares start from QAR 656. The current lowest fare is a Frontier Airlines flight departing on Fri, Nov 20; 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 QAR 579. 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.

Find Cheap Flights with Trip.com

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

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Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, 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 have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
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 according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed 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 visit the customer support pages.