Use the FlyLogan App to pre-order food and save time at BOS. Most eateries participate, ensuring your meal is ready for pick-up.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Southwest) |
One-way from | $68 (Southwest) |
Popular in | May |
Cheapest in | January |
Average price | $260 |
Good round-trip deal | $203 or less |
Good one-way deal | $136 or less |
Fly from
Fly to
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 4/28
5:45 am-7:20 am
Nonstop2h 35m
Chicago Midway
Wed 4/30
6:50 am-2:00 pm
1 stop6h 10m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/1
12:48 pm-11:39 pm
1 stop11h 51m
Chicago Midway
Sun 5/4
4:00 pm-9:34 am
1 stop16h 34m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 5/30
9:00 am-7:14 pm
1 stop11h 14m
Chicago Midway
Mon 6/2
7:00 pm-9:14 am
1 stop13h 14m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/8
5:20 am-8:40 am
1 stop4h 20m
Chicago Midway
Mon 5/12
6:25 pm-11:46 pm
1 stop4h 21m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/22
11:31 am-12:25 pm
1 stop25h 54m
Chicago Midway
Mon 5/26
8:04 pm-9:50 pm
3 stops24h 46m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 5/9
1:15 pm-5:40 pm
1 stop5h 25m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 4/28
6:00 am-12:31 pm
1 stop7h 31m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 6/8
11:31 am-7:15 am
1 stop20h 44m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 6/15
6:10 am-7:46 pm
2 stops38h 36m
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/24
4:25 pm-9:13 pm
1 stop5h 48m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars |
The price you pay for your flight from Boston to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 82 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, April is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $160). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike in the morning, when flights are generally more expensive, you can save up to 7% on flights from Boston to Chicago Midway Airport by exploring options for tickets at noon.
Travelers seeking maximum savings on their Boston to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Entertainment
Comfort
Crew
Boarding
Overall
Food
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Comfort
Crew
Boarding
Overall
Food
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Comfort
Crew
Boarding
Overall
Food
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Comfort
Crew
Boarding
Overall
Food
Reviews
Ila,Mar 2025
HOU - DAL
Entertainment
Comfort
Crew
Boarding
Overall
Food
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$76 | Average$102 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$97 | Average$276 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$100 | Average$156 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$147 | Average$253 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$237 | Average$411 | FlexibilityNo cancel fee | On-timeN/A |