Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Cheap Flights to Chicago
>
Boston to Chicago flight
>
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$ 692 and round-trip from HK$ 1,411. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Mon, Nov 16 | Frontier Airlines
      HK$ 692 HK$ 1,064
      35% off
      35% off
      HK$ 1,064 HK$ 692
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Wed, Nov 11 | Frontier Airlines
      HK$ 737 HK$ 1,064
      31% off
      31% off
      HK$ 1,064 HK$ 737
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      HK$ 772 HK$ 1,064
      27% off
      27% off
      HK$ 1,064 HK$ 772
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Wed, Dec 9 | Delta Air Lines
      HK$ 816
      23% off
      HK$ 1,064 HK$ 816
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Fri, Dec 11 | Delta Air Lines
      HK$ 850
      20% off
      HK$ 1,064 HK$ 850
    • BOS 11:55
      5h 44m
      1 stop
      MDW 16:39
      Boston - Chicago | Sat, Nov 14 | Delta Air Lines
      HK$ 851
      20% off
      HK$ 1,064 HK$ 851
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
      Find more flights
      Find more flights
    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Sun, Nov 22 | Frontier Airlines
      ORD 05:40
      27h 31m
      1 stop
      BOS 10:11
      Chicago - Boston | Wed, Nov 25 | Frontier Airlines
      HK$ 1,411 HK$ 1,882
      25% off
      25% off
      HK$ 1,882 HK$ 1,411
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      MDW 18:42
      11h 59m
      1 stop
      BOS 07:41
      Chicago - Boston | Sat, Nov 21 | Frontier Airlines
      HK$ 1,412 HK$ 1,882
      25% off
      25% off
      HK$ 1,882 HK$ 1,412
    • 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 | Wed, Nov 25 | Frontier Airlines
      HK$ 1,424 HK$ 1,882
      24% off
      24% off
      HK$ 1,882 HK$ 1,424
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Thu, Nov 26 | Frontier Airlines
      HK$ 1,426
      24% off
      HK$ 1,882 HK$ 1,426
    • BOS 10:25
      10h 5m
      1 stop
      MDW 19:30
      Boston - Chicago | Sat, Dec 19 | Frontier Airlines
      MDW 20:35
      11h 55m
      1 stop
      BOS 09:30
      Chicago - Boston | Mon, Dec 21 | Frontier Airlines
      HK$ 1,436
      24% off
      HK$ 1,882 HK$ 1,436
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
      CHI 15:00
      6h
      Direct
      BOS 16:00
      Chicago - Boston | Sat, Oct 31 | Normal Airline
      Find more flights
      Find more flights
    • BOS 05:30
      4h 20m
      1 stop
      MDW 08:50
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      HK$ 1,302 HK$ 2,862
      55% off
      55% off
      HK$ 2,862 HK$ 1,302
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      HK$ 1,375 HK$ 2,862
      52% off
      52% off
      HK$ 2,862 HK$ 1,375
    • BOS 05:30
      5h 16m
      1 stop
      MDW 09:46
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      HK$ 1,438 HK$ 2,862
      50% off
      50% off
      HK$ 2,862 HK$ 1,438
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      HK$ 1,531
      47% off
      HK$ 2,862 HK$ 1,531
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      HK$ 1,596
      44% off
      HK$ 2,862 HK$ 1,596
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
      Find more flights
      Find more flights
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Fri, Dec 11 | Delta Air Lines
      HK$ 850 HK$ 1,064
      20% off
      20% off
      HK$ 1,064 HK$ 850
    • BOS 11:55
      5h 44m
      1 stop
      MDW 16:39
      Boston - Chicago | Sat, Nov 14 | Delta Air Lines
      HK$ 851 HK$ 1,064
      20% off
      20% off
      HK$ 1,064 HK$ 851
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Wed, Dec 9 | Delta Air Lines
      HK$ 816 HK$ 1,064
      23% off
      23% off
      HK$ 1,064 HK$ 816
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      HK$ 772
      27% off
      HK$ 1,064 HK$ 772
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Mon, Nov 16 | Frontier Airlines
      HK$ 692
      35% off
      HK$ 1,064 HK$ 692
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Wed, Nov 11 | Frontier Airlines
      HK$ 737
      31% off
      HK$ 1,064 HK$ 737
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
      Find more flights
      Find more flights

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 HK$ 692) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From HK$ 692
Delta Air Lines
From HK$ 816
Hahn Air
From HK$ 1,263

Find more flights and airlines

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. DL1019

    Boston Logan International Airport

    05:30

    BOS

    2h 25m

    Direct

    07:55

    DTW

    S M T W T F S
    Search

  4. DL4684

    Detroit Metropolitan Wayne County Airport

    08:25

    DTW

    1h 24m

    Direct

    08:49

    MDW

    S M T W T F S

  5. DL2464

    Boston Logan International Airport

    18:55

    BOS

    3h 5m

    Direct

    22:00

    ATL

    - - T - - - -
    Search

  6. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  7. DL2222

    Boston Logan International Airport

    12:55

    BOS

    2h 18m

    Direct

    15:13

    DTW

    S M T W T F S
    Search

  8. DL4677

    Detroit Metropolitan Wayne County Airport

    17:40

    DTW

    1h 20m

    Direct

    18:00

    MDW

    S M T W T F S

  9. DL695

    Boston Logan International Airport

    06:45

    BOS

    3h 13m

    Direct

    09:58

    ATL

    S M T W T F S
    Search

  10. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    - - T W T - -

  11. F93511

    Boston Logan International Airport

    12:57

    BOS

    3h 7m

    Direct

    16:04

    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
Find more flights and airlines

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 HK$ 692
Cheapest return ticket price HK$ 1,411

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 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 HK$ 1,603 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 HK$ 692, and round-trip fares start from HK$ 1,411. The current lowest fare is a Frontier Airlines flight departing on Mon, Nov 16; 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$ 1,246. 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.