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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 DKK 620 and round-trip from DKK 1,208. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sun, Nov 1 | Frontier Airlines
      DKK 620 DKK 996
      38% off
      38% off
      DKK 996 DKK 620
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Tue, Dec 8 | Delta Air Lines
      DKK 698 DKK 996
      30% off
      30% off
      DKK 996 DKK 698
    • BOS 15:15
      8h 18m
      1 stop
      MDW 22:33
      Boston - Chicago | Sun, Nov 1 | Delta Air Lines
      DKK 698 DKK 996
      30% off
      30% off
      DKK 996 DKK 698
    • BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Wed, Nov 18 | Hahn Air
      DKK 712
      28% off
      DKK 996 DKK 712
    • BOS 06:20
      6h 44m
      1 stop
      MDW 12:04
      Boston - Chicago | Fri, Dec 11 | Delta Air Lines
      DKK 727
      27% off
      DKK 996 DKK 727
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Fri, Oct 30 | Normal Airline
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    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Mon, Nov 23 | Frontier Airlines
      ORD 05:40
      27h 31m
      1 stop
      BOS 10:11
      Chicago - Boston | Thu, Nov 26 | Frontier Airlines
      DKK 1,208 DKK 1,765
      32% off
      32% off
      DKK 1,765 DKK 1,208
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      MDW 18:42
      11h 59m
      1 stop
      BOS 07:41
      Chicago - Boston | Sun, Nov 22 | Frontier Airlines
      DKK 1,209 DKK 1,765
      32% off
      32% off
      DKK 1,765 DKK 1,209
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Sun, Nov 22 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Thu, Nov 26 | Frontier Airlines
      DKK 1,219 DKK 1,765
      31% off
      31% off
      DKK 1,765 DKK 1,219
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Sat, Nov 21 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Fri, Nov 27 | Frontier Airlines
      DKK 1,221
      31% off
      DKK 1,765 DKK 1,221
    • BOS 10:25
      10h 5m
      1 stop
      MDW 19:30
      Boston - Chicago | Sun, Dec 20 | Frontier Airlines
      MDW 20:35
      11h 55m
      1 stop
      BOS 09:30
      Chicago - Boston | Tue, Dec 22 | Frontier Airlines
      DKK 1,229
      30% off
      DKK 1,765 DKK 1,229
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Fri, Oct 30 | Normal Airline
      CHI 15:00
      6h
      Direct
      BOS 16:00
      Chicago - Boston | Sun, Nov 1 | Normal Airline
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    • Cheapest nonstop
      BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Wed, Nov 18 | Hahn Air
      DKK 712 DKK 996
      28% off
      28% off
      DKK 996 DKK 712
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Fri, Oct 30 | Normal Airline
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    • BOS 05:30
      4h 20m
      1 stop
      MDW 08:50
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      DKK 1,114 DKK 2,684
      57% off
      57% off
      DKK 2,684 DKK 1,114
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      DKK 1,176 DKK 2,684
      56% off
      56% off
      DKK 2,684 DKK 1,176
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      DKK 1,184 DKK 2,684
      56% off
      56% off
      DKK 2,684 DKK 1,184
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      DKK 1,613
      40% off
      DKK 2,684 DKK 1,613
    • BOS 05:30
      5h 16m
      1 stop
      MDW 09:46
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      DKK 1,702
      37% off
      DKK 2,684 DKK 1,702
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Fri, Oct 30 | Normal Airline
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    • BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Wed, Nov 18 | Hahn Air
      DKK 712 DKK 996
      28% off
      28% off
      DKK 996 DKK 712
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Tue, Dec 8 | Delta Air Lines
      DKK 698 DKK 996
      30% off
      30% off
      DKK 996 DKK 698
    • BOS 06:20
      6h 44m
      1 stop
      MDW 12:04
      Boston - Chicago | Fri, Dec 11 | Delta Air Lines
      DKK 727 DKK 996
      27% off
      27% off
      DKK 996 DKK 727
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sun, Nov 1 | Frontier Airlines
      DKK 620
      38% off
      DKK 996 DKK 620
    • BOS 15:15
      8h 18m
      1 stop
      MDW 22:33
      Boston - Chicago | Sun, Nov 1 | Delta Air Lines
      DKK 698
      30% off
      DKK 996 DKK 698
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Fri, Oct 30 | 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 DKK 660) among 6 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From DKK 660
Delta Air Lines
From DKK 698
Hahn Air
From DKK 1,031
Allegiant Air
From DKK 1,973
Jetblue Airways
From DKK 2,435
Alaska Airlines
From DKK 2,631

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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. DL2464

    Boston Logan International Airport

    18:55

    BOS

    3h 5m

    Direct

    22:00

    ATL

    - - T - - - -
    Search

  4. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    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. DL695

    Boston Logan International Airport

    06:45

    BOS

    3h 13m

    Direct

    09:58

    ATL

    S M T W T F S
    Search

  8. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    - - T W T - -

  9. DL1019

    Boston Logan International Airport

    05:30

    BOS

    2h 25m

    Direct

    07:55

    DTW

    S M T W T F S
    Search

  10. DL4684

    Detroit Metropolitan Wayne County Airport

    08:25

    DTW

    1h 24m

    Direct

    08:49

    MDW

    S M T W T F S

  11. F93511

    Boston Logan International Airport

    12:39

    BOS

    3h 20m

    Direct

    15:59

    ATL

    S M T W T F S
    Search

  12. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  13. DL1710

    Boston Logan International Airport

    15:10

    BOS

    3h 1m

    Direct

    18:11

    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. DL2330

    Boston Logan International Airport

    16:20

    BOS

    3h 3m

    Direct

    19:23

    ATL

    S M T W T F S
    Search

  16. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  17. F93511

    Boston Logan International Airport

    12:39

    BOS

    3h 20m

    Direct

    15:59

    ATL

    S M T W T F S
    Search

  18. 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 DKK 620
Cheapest return ticket price DKK 1,208

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 6 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 4 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 DKK 1,719 in November, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 05:20 and arrives in Chicago Midway International Airport (MDW) at 06:55.
  • The latest flight departs from Boston Logan International Airport (BOS) at 18:35 and arrives in Chicago Midway International Airport (MDW) at 20:20.
    • 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 DKK 620, and round-trip fares start from DKK 1,208. The current lowest fare is a Frontier Airlines flight departing on Sun, Nov 1; 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 DKK 1,066. 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.

Most popular destination

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

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, regulatory fees, etc) with all fees confirmed before payment. Fees for baggage, 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 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.