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Good to Know
Low Season:
September
Best time to beat the crowds
2%
expected price decrease
High Season:
April
Most popular time to fly
5%
expected price increase
Average Price:
$217
(avg. price over the last 2 weeks)
Good Deal:
$147
or less (round trip)
When to Book Flights from Boston to Chicago
Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days
Top Tips for Finding a Cheap Flight
Looking for a cheap flight? 25% of our users found flights on this route for $146 or less.
The cheapest flight from Boston to Chicago was found 89 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be March, April and May. The cheapest month to fly is September.
Morning departure is around 10% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days
Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal's Test Kitchen. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport, this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at BeRelax? Located in Terminal C near Gare C-25 at Boston Logan International Airport, BeRelax also offers waxing and facial care to give you your best look and most relaxed self before your flight.
Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access, and even a Starbucks coffee shop.