Travelers have found it’s best to book a flight 55 days in advance to save up to 24% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 55 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Boston to Illinois 1-2 weeks in advance for as low as $237, or $310 for flights within the next 24 hours.
The best pricing can be found in the month of January. Prices to Illinois from Boston average $260. You can even find prices in January for less than $260, as users have found deals to Illinois from as low as $79. The month of June appears to be one of the more expensive times to travel to Illinois from Boston. Flying in the targeted month can save you up to 37%.
When flying from Boston to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$95 - $165
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/27
1 stop11h 00m
Chicago Midway
Sat 5/11
1 stop10h 51m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 4/10
1 stop11h 37m
Chicago Midway
Mon 4/15
1 stop15h 24m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 4/9
1 stop6h 08m
Chicago Midway
Sat 4/13
1 stop10h 51m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/4
1 stop13h 36m
Chicago O'Hare Intl
Tue 4/9
1 stop8h 20m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/6
1 stop27h 26m
Chicago O'Hare Intl
Thu 5/9
1 stop13h 02m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/7
Nonstop2h 54m
Chicago O'Hare Intl
Tue 5/14
Nonstop2h 35m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/4
Nonstop2h 53m
Chicago O'Hare Intl
Wed 5/8
Nonstop2h 26m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/29
Nonstop2h 50m
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 20m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 4/9
Nonstop3h 11m
Chicago O'Hare Intl
Wed 4/10
Nonstop2h 14m
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
No tray tables for food or drink not convenient nor comfortable
31%of flight departures | Early morningMidnight to 6 am |
---|---|
28%of flight departures | Morning6 am to noon |
36%of flight departures | AfternoonNoon to 6 pm |
5%of flight departures | Evening6 pm to midnight |
Cheapflights makes it easy to find Boston to Illinois flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Illinois from Boston.
Certainly. Search results for flights to Illinois from Boston shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Not ready to book yet? You can track prices for flights from Boston to Illinois on Cheapflights with our Price Alert feature and get notified when better prices are available.