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Cheap flights from Boston to Chicago Midway (BOS - MDW)

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The best prices from Boston to Chicago Midway are usually found in August or February, booked 22 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

How to find the cheapest flight from
Boston (BOS) to Chicago Midway (MDW)

BOS - MDW
Price
$109 - $480
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches

Popular in

June

High demand for flights, 47% potential price rise

Cheapest in

August

Best time to find cheap flights, 57% potential price drop

Average price

$246

Average for round-trip flights in October 2020

Round-trip from

$109

From Boston to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Boston to Chicago Midway?

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago Midway. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Boston to Chicago Midway?

To save on the cost of your flight from Boston to Chicago Midway, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

What is the cheapest month to fly from Boston to Chicago Midway?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago Midway. Flights to Chicago Midway from Boston in April are about $135 on average during April, but can be found for as low as $33.

When is the cheapest time to fly from Boston to Chicago Midway (BOS - MDW)?

Unlike in the afternoon, when flights are generally more expensive, you can save up to 7% on flights from Boston to Chicago Midway by exploring options for tickets at noon.

Cheap flights from Boston to Chicago Midway in October, November 2020

The best prices found for BOS to MDW flights for October, November
4 Nov - 11 Nov
$106pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
10 Nov - 12 Nov
$112pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
20 Nov - 23 Nov
$118pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl

Boston to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Boston found for this year
4 Dec - 6 Dec
$106pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
10 Nov - 12 Nov
$112pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
20 Nov - 23 Nov
$118pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl

Last minute flights from Boston to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Boston, departing today and this week
4 Nov - 11 Nov
$106pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
6 Nov - 12 Nov
$112pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl
6 Nov - 8 Nov
$118pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl

One-way flights to Chicago Midway from Boston

The cheapest one-way flights from Boston to Chicago Midway
5:15 am - 12:48 pm
Allegiant Air
1 Stop
8h 33m
BOS - MDW
Allegiant Air
$115
Kiwi.com
11:46 am - 12:48 pm
Multiple Airlines
3 Stops
50h 02m
BOS - MDW
Multiple Airlines
$146
KAYAK
2:15 am - 11:50 am
Delta
1 Stop
10h 35m
BOS - MDW
Delta
$148
Delta

Related info for your journey

Useful info, stats and facts about Boston to Chicago Midway flights.

Flight FAQs

From Boston to Chicago Midway

Are flight prices decreasing from Boston to Chicago Midway due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Boston and Chicago Midway for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Boston Logan Intl to Chicago Midway to control the spread of COVID-19?

New policies can now be found on JetBlue, Southwest, and Delta to help keep travelers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Boston Logan Intl to Chicago Midway. Policies will vary by airline.

Which airlines flying from Boston Logan Intl to Chicago Midway have flexible cancellations due to COVID-19?

Some of our airline partners flying from Boston Logan Intl to Chicago Midway have new flexible policies in place due to COVID-19. Delta, United Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

Can I find flights from Boston to Chicago Midway for under $200 on Cheapflights?

Yes, there are multiple flights from Boston to Chicago Midway for under $200. The cheapest flight booked recently is on Delta for just $106, but on average you can expect to pay $153.

Are there nonstop flights from Boston to Chicago Midway for under $100 on Cheapflights?

There are no nonstop flights from Boston to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Boston to Chicago Midway for under $200?

There are currently 20+ open flights from Boston to Chicago Midway within the next 7 days for less than $200.

What days are nonstop flights available from Boston to Chicago Midway?

Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Boston to Chicago Midway on average per day?

Travelers can expect 2 flights from Boston Logan Intl to Chicago Midway on average per day.
Early Morning (Midnight to 6am) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

Does it rain more in Boston or Chicago Midway?

Boston will have greater rainfall in 0 compared to Chicago Midway over the next 12 days.

Is Boston weather warmer or cooler than Chicago Midway?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago Midway are the same as in Boston.

How long is the flight from Boston to Chicago Midway?

Departing from Boston to Chicago Midway will take you 5h 20m. The distance from Boston to Chicago Midway is about 863 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Boston to Chicago Midway round-trip?

Currently priced at $106, Delta will fly you from Boston to Chicago Midway and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Allegiant Air for as low as $177. Users have found that Delta is 58% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Boston to Chicago Midway one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $53. Delta is not the only option available. At the moment, Allegiant Air is another option, for $84.

Alternative routes for Boston to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Boston to Chicago Midway
Average temperature for October in Chicago Midway
64.4 °F
Avg rainfall for October in Chicago Midway
2.6 ″

Airports servicing Boston

Airports servicing Chicago

Hourly flight availability from Boston to Chicago Midway

Early morning Midnight to 6 AM 50% of BOS to MDW departures
Afternoon Noon to 6 PM 50% of BOS to MDW departures
Morning 6 AM to noon 0% of BOS to MDW departures
Evening 6 PM to midnight 0% of BOS to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Boston to Chicago Midway
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights