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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 TRY 4,381 and round-trip from TRY 8,963. Based on Trip.com's latest 7-day flight data.

    • BOS 11:06 AM
      9h 41m
      1 stop
      MDW 7:47 PM
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      MDW 8:42 PM
      12h 29m
      1 stop
      BOS 10:11 AM
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      TRY 8,963 TRY 12,971
      31% off
      31% off
      TRY 12,971 TRY 8,963
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Wed, Nov 18 | Frontier Airlines
      MDW 8:42 PM
      12h 29m
      1 stop
      BOS 10:11 AM
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      TRY 9,045 TRY 12,971
      30% off
      30% off
      TRY 12,971 TRY 9,045
    • BOS 12:15 PM
      6h 32m
      1 stop
      MDW 5:47 PM
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      MDW 8:42 PM
      12h 29m
      1 stop
      BOS 10:11 AM
      Chicago - Boston | Tue, Nov 24 | Frontier Airlines
      TRY 9,045 TRY 12,971
      30% off
      30% off
      TRY 12,971 TRY 9,045
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      ORD 5:40 AM
      27h 31m
      1 stop
      BOS 10:11 AM
      Chicago - Boston | Mon, Nov 23 | Frontier Airlines
      TRY 9,418
      27% off
      TRY 12,971 TRY 9,418
    • BOS 12:15 PM
      6h 32m
      1 stop
      MDW 5:47 PM
      Boston - Chicago | Tue, Nov 10 | Frontier Airlines
      ORD 1:00 PM
      2h 49m
      Nonstop
      BOS 4:49 PM
      Chicago - Boston | Thu, Nov 12 | Jetblue Airways
      TRY 9,598
      26% off
      TRY 12,971 TRY 9,598
    • BOS 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Boston - Chicago | Mon, Oct 26 | Normal Airline
      CHI 3:00 PM
      6h
      Nonstop
      BOS 4:00 PM
      Chicago - Boston | Wed, Oct 28 | Normal Airline
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    • Cheapest
      BOS 11:06 AM
      9h 41m
      1 stop
      MDW 7:47 PM
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      TRY 4,381 TRY 7,211
      39% off
      39% off
      TRY 7,211 TRY 4,381
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Wed, Nov 18 | Frontier Airlines
      TRY 4,627 TRY 7,211
      36% off
      36% off
      TRY 7,211 TRY 4,627
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      TRY 4,672 TRY 7,211
      35% off
      35% off
      TRY 7,211 TRY 4,672
    • BOS 12:15 PM
      6h 32m
      1 stop
      MDW 5:47 PM
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      TRY 4,971
      31% off
      TRY 7,211 TRY 4,971
    • BOS 6:45 AM
      6h 14m
      1 stop
      MDW 11:59 AM
      Boston - Chicago | Tue, Nov 17 | Delta Air Lines
      TRY 5,321
      26% off
      TRY 7,211 TRY 5,321
    • BOS 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Boston - Chicago | Mon, Oct 26 | Normal Airline
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    • BOS 1:04 PM
      5h 40m
      1 stop
      MDW 5:44 PM
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      TRY 8,202 TRY 12,163
      33% off
      33% off
      TRY 12,163 TRY 8,202
    • BOS 1:04 PM
      5h 40m
      1 stop
      MDW 5:44 PM
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      TRY 8,202 TRY 12,163
      33% off
      33% off
      TRY 12,163 TRY 8,202
    • BOS 5:30 AM
      4h 20m
      1 stop
      MDW 8:50 AM
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      TRY 8,254 TRY 12,163
      32% off
      32% off
      TRY 12,163 TRY 8,254
    • BOS 9:05 AM
      4h 56m
      1 stop
      MDW 1:01 PM
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      TRY 8,717
      28% off
      TRY 12,163 TRY 8,717
    • BOS 5:30 AM
      5h 16m
      1 stop
      MDW 9:46 AM
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      TRY 9,000
      26% off
      TRY 12,163 TRY 9,000
    • BOS 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Boston - Chicago | Mon, Oct 26 | Normal Airline
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    • BOS 6:45 AM
      6h 14m
      1 stop
      MDW 11:59 AM
      Boston - Chicago | Tue, Nov 17 | Delta Air Lines
      TRY 5,321 TRY 7,211
      26% off
      26% off
      TRY 7,211 TRY 5,321
    • BOS 12:15 PM
      6h 32m
      1 stop
      MDW 5:47 PM
      Boston - Chicago | Tue, Nov 17 | Frontier Airlines
      TRY 4,971 TRY 7,211
      31% off
      31% off
      TRY 7,211 TRY 4,971
    • BOS 11:06 AM
      9h 41m
      1 stop
      MDW 7:47 PM
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      TRY 4,381 TRY 7,211
      39% off
      39% off
      TRY 7,211 TRY 4,381
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Wed, Nov 18 | Frontier Airlines
      TRY 4,627
      36% off
      TRY 7,211 TRY 4,627
    • BOS 12:39 PM
      12h 8m
      1 stop
      MDW 11:47 PM
      Boston - Chicago | Mon, Nov 9 | Frontier Airlines
      TRY 4,672
      35% off
      TRY 7,211 TRY 4,672
    • BOS 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      Boston - Chicago | Mon, Oct 26 | 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 TRY 4,590) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From TRY 4,590
Delta Air Lines
From TRY 5,172
Hahn Air
From TRY 5,277

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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

    9:00 AM

    BOS

    2h 26m

    Nonstop

    11:26 AM

    DTW

    S M T W T F S
    Search

  2. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28 PM

    DTW

    1h 19m

    Nonstop

    12:47 PM

    MDW

    S M T W T F S

  3. DL1019

    Boston Logan International Airport

    5:30 AM

    BOS

    2h 25m

    Nonstop

    7:55 AM

    DTW

    S M T W T F S
    Search

  4. DL4684

    Detroit Metropolitan Wayne County Airport

    9:10 AM

    DTW

    1h 36m

    Nonstop

    9:46 AM

    MDW

    S M T W T F S

  5. DL1103

    Boston Logan International Airport

    11:29 AM

    BOS

    3h 26m

    Nonstop

    1:55 PM

    MSP

    S M T W T F S
    Search

  6. DL4714

    Minneapolis-Saint Paul International Airport

    3:08 PM

    MSP

    1h 39m

    Nonstop

    4:47 PM

    MDW

    S M T W T F S

  7. DL2222

    Boston Logan International Airport

    12:55 PM

    BOS

    2h 18m

    Nonstop

    3:13 PM

    DTW

    S M T W T F S
    Search

  8. DL4677

    Detroit Metropolitan Wayne County Airport

    5:40 PM

    DTW

    1h 20m

    Nonstop

    6:00 PM

    MDW

    S M T W T F S

  9. DL2464

    Boston Logan International Airport

    6:55 PM

    BOS

    3h 5m

    Nonstop

    10:00 PM

    ATL

    S M T - - - S
    Search

  10. DL1076

    Hartsfield–Jackson Atlanta International Airport

    10:59 PM

    ATL

    1h 56m

    Nonstop

    11:55 PM

    MDW

    S M T W T F S

  11. DL695

    Boston Logan International Airport

    6:45 AM

    BOS

    3h 13m

    Nonstop

    9:58 AM

    ATL

    S M T W T F S
    Search

  12. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00 AM

    ATL

    1h 56m

    Nonstop

    11:56 AM

    MDW

    S M T W T - S

  13. F93511

    Boston Logan International Airport

    12:57 PM

    BOS

    3h 7m

    Nonstop

    4:04 PM

    ATL

    S M T W T F S
    Search

  14. F92779

    Hartsfield–Jackson Atlanta International Airport

    4:44 PM

    ATL

    2h 1m

    Nonstop

    5:45 PM

    MDW

    - M T W T F S

  15. DL1710

    Boston Logan International Airport

    3:10 PM

    BOS

    3h 1m

    Nonstop

    6:11 PM

    ATL

    S M T W T F S
    Search

  16. DL1076

    Hartsfield–Jackson Atlanta International Airport

    10:59 PM

    ATL

    1h 56m

    Nonstop

    11:55 PM

    MDW

    S M T W T F S

  17. F93511

    Boston Logan International Airport

    12:57 PM

    BOS

    3h 7m

    Nonstop

    4:04 PM

    ATL

    S M T W T F S
    Search

  18. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:45 PM

    ATL

    1h 58m

    Nonstop

    11:43 PM

    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 1,380.83 km
Cheapest one-way ticket price TRY 4,381
Cheapest return ticket price TRY 8,963

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 TRY 12,933 in November, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 06:20 and arrives in Chicago Midway International Airport (MDW) at 08:15.
  • The latest flight departs from Boston Logan International Airport (BOS) at 20:05 and arrives in Chicago Midway International Airport (MDW) at 21:55.
    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • 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 TRY 4,381, and round-trip fares start from TRY 8,963. 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 TRY 7,898. 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.

Popular Destinations

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, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, 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.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled 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 check the customer support pages.