Cheap flights from Boston to Chicago from $49
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 5/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
Find the cheapest one-way flights from Boston to Chicago
If you're looking for one-way flights from Boston to Chicago, view some of our deals below provided by American Airlines, Frontier and Southwest
Search last-minute flights to Chicago from Boston
Find and compare round-trip flight prices for your last-minute flight from Boston to Chicago
Best airlines flying from Boston to Chicago
Compare and see reviews for airlines that fly from Boston to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $39 | Free Cancellation | Rating 8.0 9,115 reviews | |||
| PriceFrom $79 | Free Cancellation | Rating 7.6 4,606 reviews | |||
| PriceFrom $89 | Free Cancellation | Rating 7.4 11,228 reviews | |||
| PriceFrom $94 | Free Cancellation | Rating 8.0 10,966 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 6.3 4,132 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 7.3 14,889 reviews | |||
| PriceFrom $112 | Free Cancellation | Rating 6.4 8,746 reviews |
Alaska Airlines Flights From Boston to Chicago
The lowest priced Alaska Airlines flight from Boston to Chicago from the last 72 hours was $39. Generally, Alaska Airlines has 28 flights on this route every week with an average price of $94. Alaska Airlines is rated 8.0/10 by our users.
Delta Flights From Boston to Chicago
Delta is also a popular choice for this route. Delta flight deals for Boston to Chicago start from as low as $94 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $371. Delta operates 28 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 10,966 reviews.
JetBlue flights from Boston to Chicago
Our best JetBlue deals on Boston to Chicago flight tickets
Delta flights from Boston to Chicago
Our best Delta deals on Boston to Chicago flight tickets
How to get the cheapest flight ticket from Boston to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly from Boston to Chicago?
January. The cheapest time of year to fly to Chicago from Boston is January. Most expensive is June
What is the cheapest day to depart Boston for Chicago?
Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday
When is the cheapest time to fly from Boston to Chicago?
In the evening. Boston to Chicago flights are approximately 10% more expensive at noon than in the evening
What is the cheapest airline that flies to Chicago from Boston?
Alaska Airlines. Alaska Airlines, American Airlines, and Frontier are the most popular carriers operating from Boston to Chicago
What is the cheapest Boston to Chicago flight route?
Boston Logan Intl - Chicago O'Hare Intl. Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices
How far in advance should you book Boston to Chicago flights?
54 days before. The cheapest time to buy a flight from Boston to Chicago is approximately 54 days to departure
How many flights depart from Boston to Chicago on average per day?
51 flights are operational weekly from Boston to Chicago as of April 2024. The most popular departure time for this route is 7:00AM, with 55% of flights per day taking off in the afternoon.
How many flights depart from Boston to Chicago on average per week?
As of April 2024, 363 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Monday, with 18% of weekly flights taking off on this day.
What cabin class options are available on Boston to Chicago flights?
There are 4 cabin classes available to choose from on Boston to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Boston to Chicago flights?
No. A direct flight is the cheapest option for a flight between Boston to Chicago.
Cheap Boston to Chicago (BOS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Best Price Found | $49 |
|---|---|
Fastest flight time | 2h 30m |
Direct flights | Every day |
Airports in Chicago | 2 airports |
Is flying the fastest way to get from Boston to Chicago?
To save time, the fastest way to travel is by flight from Boston to Chicago on Southwest. Expect the length of time you’ll spend onboard Southwest to be about 2h 30m compared to taking a train from Boston to Chicago or a bus from Boston to Chicago which have been found to be slower alternatives.
Is flying the cheapest way to get from Boston to Chicago?
The cheapest way is to get a flight from Boston to Chicago, which can be as cheap as $73. A train from Boston to Chicago is more expensive than a flight, with prices starting at $263. A bus from Boston to Chicago is also an option, with an average price of $204.
How far is Boston Logan Intl to Chicago by plane?
A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 30m is a normal flight duration for this route.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?
Prices for flights from Boston Logan Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There are 8 operators available for flights from Boston Logan Intl Airport to Chicago as of April 2024.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Why use momondo?
Why should I use momondo to find a flight deal from Boston to Chicago?
It is quick and easy to find Boston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Boston to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Boston to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.