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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 OMR 34 and round-trip from OMR 70. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      OMR 34 OMR 48
      28% off
      28% off
      OMR 48 OMR 34
    • Cheapest
      BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Nov 14 | Frontier Airlines
      OMR 34 OMR 48
      28% off
      28% off
      OMR 48 OMR 34
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      OMR 37 OMR 48
      23% off
      23% off
      OMR 48 OMR 37
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      OMR 38
      21% off
      OMR 48 OMR 38
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      OMR 40
      17% off
      OMR 48 OMR 40
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Wed, Dec 9 | Delta Air Lines
      OMR 42
      13% off
      OMR 48 OMR 42
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Sat, Nov 21 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Tue, Nov 24 | Frontier Airlines
      OMR 70 OMR 85
      18% off
      18% off
      OMR 85 OMR 70
    • 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 | Tue, Nov 24 | Frontier Airlines
      OMR 70 OMR 85
      18% off
      18% off
      OMR 85 OMR 70
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Wed, Nov 18 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Wed, Nov 25 | Frontier Airlines
      OMR 70 OMR 85
      18% off
      18% off
      OMR 85 OMR 70
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      ORD 05:40
      27h 31m
      1 stop
      BOS 10:11
      Chicago - Boston | Tue, Nov 24 | Frontier Airlines
      OMR 73
      14% off
      OMR 85 OMR 73
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Wed, Nov 11 | Frontier Airlines
      ORD 13:00
      2h 49m
      Direct
      BOS 16:49
      Chicago - Boston | Fri, Nov 13 | Jetblue Airways
      OMR 75
      12% off
      OMR 85 OMR 75
    • 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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    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      OMR 64 OMR 80
      20% off
      20% off
      OMR 80 OMR 64
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      OMR 64 OMR 80
      20% off
      20% off
      OMR 80 OMR 64
    • BOS 05:30
      4h 20m
      1 stop
      MDW 08:50
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      OMR 64 OMR 80
      20% off
      20% off
      OMR 80 OMR 64
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      OMR 68
      15% off
      OMR 80 OMR 68
    • BOS 05:30
      5h 16m
      1 stop
      MDW 09:46
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      OMR 71
      11% off
      OMR 80 OMR 71
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Wed, Dec 9 | Delta Air Lines
      OMR 42 OMR 48
      13% off
      13% off
      OMR 48 OMR 42
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      OMR 40 OMR 48
      17% off
      17% off
      OMR 48 OMR 40
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      OMR 38 OMR 48
      21% off
      21% off
      OMR 48 OMR 38
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Nov 14 | Frontier Airlines
      OMR 34
      28% off
      OMR 48 OMR 34
    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      OMR 34
      28% off
      OMR 48 OMR 34
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      OMR 37
      23% off
      OMR 48 OMR 37
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Tue, Oct 27 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

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 OMR 34) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From OMR 34
Delta Air Lines
From OMR 42
Hahn Air
From OMR 57

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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
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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 OMR 34
Cheapest return ticket price OMR 70

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 OMR 101 in November, 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 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 OMR 34, and round-trip fares start from OMR 70. 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 OMR 62. 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 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

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to 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 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.