Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
>
Boston to Chicago flight
>
Boston Logan International Airport to Chicago Midway International Airport flight

Search for flights from Boston to Chicago and check out affordable one-way and round-trip options.

      • BOS 5:51 AM
        8h 28m
        1 stop
        MDW 1:19 PM
        Boston - Chicago | Sun, May 10 | Delta Air Lines
        ORD 7:15 PM
        2h 34m
        Nonstop
        BOS 10:49 PM
        Chicago - Boston | Wed, May 13 | Delta Air Lines
        CAD 151 CAD 252
        40% off
        40% off
        CAD 252 CAD 151
      • BOS 5:51 AM
        8h 28m
        1 stop
        MDW 1:19 PM
        Boston - Chicago | Sun, May 31 | Delta Air Lines
        MDW 6:36 PM
        3h 53m
        1 stop
        BOS 11:29 PM
        Chicago - Boston | Tue, Jun 2 | Delta Air Lines
        CAD 188 CAD 252
        25% off
        25% off
        CAD 252 CAD 188
      • BOS 9:05 AM
        4h 37m
        1 stop
        MDW 12:42 PM
        Boston - Chicago | Thu, May 28 | Delta Air Lines
        ORD 6:06 PM
        6h 22m
        1 stop
        BOS 1:28 AM
        Chicago - Boston | Tue, Jun 2 | Delta Air Lines
        CAD 189 CAD 252
        25% off
        25% off
        CAD 252 CAD 189
      • BOS 12:05 PM
        6h 51m
        1 stop
        MDW 5:56 PM
        Boston - Chicago | Wed, Jun 3 | Delta Air Lines
        MDW 6:36 PM
        3h 53m
        1 stop
        BOS 11:29 PM
        Chicago - Boston | Thu, Jun 4 | Delta Air Lines
        CAD 191
        24% off
        CAD 252 CAD 191
      • BOS 5:40 AM
        4h 3m
        1 stop
        MDW 8:43 AM
        Boston - Chicago | Thu, May 14 | Delta Air Lines
        ORD 7:05 AM
        6h 10m
        1 stop
        BOS 2:15 PM
        Chicago - Boston | Thu, May 21 | Delta Air Lines
        CAD 192
        24% off
        CAD 252 CAD 192
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI Invalid Date
        Boston - Chicago | Mon, Apr 27 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        BOS 4:00 PM
        Chicago - Boston | Wed, Apr 29 | Normal Airline
        Find more flights
        Find more flights
      • Cheapest nonstop
        BOS 10:45 AM
        2h 40m
        Nonstop
        MDW 12:25 PM
        Boston - Chicago | Wed, May 20 | Hahn Air
        CAD 87 CAD 151
        42% off
        42% off
        CAD 151 CAD 87
      • BOS 6:20 PM
        2h 50m
        Nonstop
        MDW 8:10 PM
        Boston - Chicago | Wed, May 13 | Hahn Air
        CAD 87 CAD 151
        42% off
        42% off
        CAD 151 CAD 87
      • BOS 6:55 PM
        2h 50m
        Nonstop
        MDW 8:45 PM
        Boston - Chicago | Thu, May 7 | Hahn Air
        CAD 95 CAD 151
        37% off
        37% off
        CAD 151 CAD 95
      • BOS 6:45 PM
        2h 50m
        Nonstop
        MDW 8:35 PM
        Boston - Chicago | Thu, Jun 4 | Hahn Air
        CAD 104
        31% off
        CAD 151 CAD 104
      • BOS 10:40 AM
        2h 40m
        Nonstop
        MDW 12:20 PM
        Boston - Chicago | Fri, May 8 | Hahn Air
        CAD 116
        23% off
        CAD 151 CAD 116
      • BOS 6:45 AM
        6h 15m
        1 stop
        MDW 12:00 PM
        Boston - Chicago | Tue, Jun 9 | Delta Air Lines
        CAD 108
        28% off
        CAD 151 CAD 108
      • BOS 1:00 PM
        17h 25m
        1 stop
        CHI Invalid Date
        Boston - Chicago | Mon, Apr 27 | 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.

Selected Airlines from Boston Logan International Airport to Chicago Midway International Airport

See which airlines fly from Boston to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Hahn Air
From CAD 87
Delta Air Lines
From CAD 108
Frontier Airlines
From CAD 127

Find more flights and airlines

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. F93085

    Boston Logan International Airport

    6:00 AM

    BOS

    3h 18m

    Nonstop

    9:18 AM

    ATL

    S M T W T F S
    Search

  2. F92291

    Hartsfield-Jackson Atlanta International Airport

    9:05 PM

    ATL

    2h 6m

    Nonstop

    10:11 PM

    MDW

    S M T W T F S

  3. F93085

    Boston Logan International Airport

    6:00 AM

    BOS

    3h 18m

    Nonstop

    9:18 AM

    ATL

    S M T W T F S
    Search

  4. F92779

    Hartsfield-Jackson Atlanta International Airport

    9:59 AM

    ATL

    1h 59m

    Nonstop

    10:58 AM

    MDW

    S M T W T F S

  5. DL695

    Boston Logan International Airport

    6:55 AM

    BOS

    3h 8m

    Nonstop

    10:03 AM

    ATL

    S M T W T F S
    Search

  6. DL2417

    Hartsfield-Jackson Atlanta International Airport

    11:00 AM

    ATL

    1h 56m

    Nonstop

    11:56 AM

    MDW

    S M T W T - S
Find more flights and airlines

Boston Logan International Airport to Chicago Midway International Airport Flights Info

Flight distance1,380.83 km
Cheapest one-way ticket priceCAD 87
Cheapest return ticket priceCAD 151

FAQs for Boston Logan International Airport to Chicago Midway International Airport Flights

  • How long is a flight from Boston Logan International Airport to Chicago Midway International Airport?

    It takes around 2 hours 42 minutes to fly from Boston Logan International Airport (bos) to Chicago Midway International Airport (mdw).
  • There are around 4 daily flights from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW).
  • Tickets cost around CAD 230 in May, making it the cheapest month to book. Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.
  • 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 CAD 272 in April, 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 Chicago 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 Chicago O'Hare International Airport. The distance is around 25 km.

Popular Destinations

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, 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.