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BOS - CHI
Find cheap flights from Boston to Chicago
Round-trip
Economy
Search hundreds of travel sites at once for deals on flights to Chicago
Good to know
Low season |
September | Best time to beat the crowds with an average 17% drop in price. |
|---|---|---|
High season |
July | Most popular time to fly with an average 15% increase in price. |
Average price of a round-trip |
$190 | (avg. price over the last 2 weeks) |
Good deal for a round-trip |
$173 | or less |
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 $104 or less.
- The cheapest flight from Boston to Chicago was found 88 days before departure, on average.
- Book at least 5 weeks before departure in order to get a below-average price.
- High season is considered to be June, July and August. The cheapest month to fly is September.
- Morning departure is around 111% more expensive than an evening flight, on average*.
- 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.
FAQs for booking Boston to Chicago flights
Which airlines have a flexible cancellation policy for flights from Boston Logan Intl to Chicago due to COVID-19?
Which airlines apply social distancing measures on flights from Boston Logan Intl to Chicago due to COVID-19?
How long does a flight from Boston to Chicago take?
How many flights are there between Boston and Chicago?
Which airlines provide the cheapest flights from Boston to Chicago?
Do I need a passport to fly between Boston and Chicago?
Which airlines fly most frequently between Boston and Chicago?
What’s the cheapest day of the week to fly Boston to Chicago?
Which airports will I be using when flying from Boston to Chicago?
If I want to use mass transit to get to Boston Logan International Airport, what is my best choice?
Are there pet relief areas at Boston Logan International Airport?
If I am being picked up at Chicago O'Hare International Airport, where is the best place to meet my ride?
Where can I rent a car at Chicago O'Hare International Airport?
How does KAYAK find such low prices on flights from Boston to Chicago?
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What is the Hacker Fare option on flights from Boston to Chicago?
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Chicago?
Top 4 airlines serving Boston Logan Intl to Chicago
Scores according to KAYAK customer reviews
8.2
JetBlue
Overall score based on 19,205 reviews
8.3
Boarding
8.3
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
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Boston - Chicago Flights
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.
We attempt to get accurate prices, however, prices are not guaranteed.
We attempt to get accurate prices, however, prices are not guaranteed.
Here's why:
We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.
We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.
Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.
If you have more questions or if you have a bad price to report to us,
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last
72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may
not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags.
Please check the carriers' sites.
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