Cheap flights from Boston to Chicago from $62
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 6/18. 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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Allegiant Air flights from Boston to Chicago Midway Airport
Our best Allegiant Air deals on Boston to Chicago Midway Airport flight tickets
Frontier flights from Boston to Chicago Midway Airport
Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Boston to Chicago Midway Airport
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 to Chicago Midway Airport?
The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Boston, with most prices found around $200. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Boston during the month September is also very affordable. Most momondo users find prices during this month for around $213.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Boston. The lowest ticket price found for a Thursday departure recently was $313. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $435.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Boston at noon is the least expensive time of day to depart. momondo users have found prices as low as $333 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $360. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Boston Logan Intl to Chicago Midway flight route?
Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Boston when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $257 when searching 7 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Boston for as low as $183 on momondo.
What cabin class options are available on Boston Logan Intl to Chicago Midway flights?
There are 1 cabin classes available to choose from on Boston Logan Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Boston Logan Intl to Chicago Midway?
Southwest, Allegiant Air, and Frontier are the most popular carriers operating from Boston Logan Intl to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from Boston according to our data. Southwest is the first choice among our users, with 91% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Boston to Chicago Midway Airport on average per day?
The number of flights available between Boston and Chicago Midway Airport is 4 per day as of June 2025. The most frequent departure time is 5:00AM, with 33% of daily flights leaving in the afternoon.
How many flights depart from Boston to Chicago Midway Airport on average per week?
31 flights are operational weekly from Boston to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.
When to book flights from Boston to Chicago Midway Airport
Cheap Boston to Chicago Midway Airport (BOS to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago Midway Airport
How far is Boston Logan Intl to Chicago Midway by plane?
The distance between Boston Logan Intl and Chicago Midway is about 854.8 mi. A reasonable flight in good conditions will take 2h 30m.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago Midway Airport?
Prices for flights from Boston Logan Intl Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago Midway Airport?
As of June 2025, there are 6 operators available to choose from for flights from Boston Logan Intl Airport to Chicago Midway Airport.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Boston to Chicago Midway Airport?
Based on momondo bookings for flights between Boston and Chicago Midway Airport, the leading plane model is Boeing 737-800, making up 21.44% of the total bookings. Other popular models include Boeing 737 MAX 8 with 18.74%, Boeing 737-900 with 8.81%, and Embraer 175 with 8.40%.
What is the most popular airline from Boston to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Boston to Chicago Midway Airport is Southwest, representing 84% of all bookings. The subsequent popular airlines are Delta at 7%, Frontier at 3%, and United Airlines at 2%.
Best airlines flying from Boston to Chicago Midway Airport
Compare and see reviews for airlines that fly from Boston to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $76 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $127 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $187 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $227 | Free Cancellation | Rating 8.0 7,946 reviews |
Southwest Flights From Boston to Chicago Midway Airport
Southwest flies from Boston to Chicago Midway Airport around 31 times per week, with 4,287 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $127 (round-trip), much lower than the average airfare cost of $256 for Southwest flights on this route.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Boston to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Boston.
Can I find flights from Boston to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Boston with this policy.
How can momondo help me find flights from Boston to Chicago?
Once you have performed a search for Boston to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Boston. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.