Cheap flights from Chicago Midway Airport to Boston from $59
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Boston departing on 6/1. 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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Southwest flights from Chicago Midway Airport to Boston
Our best Southwest deals on Chicago Midway Airport to Boston flight tickets
Allegiant Air flights from Chicago Midway Airport to Boston
Our best Allegiant Air deals on Chicago Midway Airport to Boston flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to Boston
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 Boston?
In general, January is the cheapest month to fly from Chicago Midway Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $185. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago Midway Airport during March instead. Flights to Boston in March, while not as cheap as those in January, still average around $237.
What is the cheapest day to depart on your flight to Boston?
The cheapest day to depart from Chicago Midway Airport to Boston is on a Wednesday when prices can be found for as low as $250. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $326.
What is the cheapest time of day to depart on your flight to Boston?
According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago Midway Airport to Boston in the evening for as low as $199. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $297 per ticket.
What is the cheapest Chicago Midway to Boston Logan Intl flight route?
Fly from Chicago Midway to Boston Logan Intl for the best Chicago Midway - Boston Logan Intl flight prices
How far in advance should I book a flight to Boston?
You are more likely to see cheaper flights to Boston from Chicago Midway Airport when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $280 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago Midway Airport for as low as $193 on momondo.
What cabin class options are available on Chicago Midway to Boston Logan Intl flights?
There are 1 cabin classes available to choose from on Chicago Midway to Boston Logan Intl 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 Chicago Midway to Boston Logan Intl?
Southwest, Allegiant Air, and Frontier are the most popular carriers operating from Chicago Midway to Boston Logan Intl
What airlines fly to Boston?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Boston from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 86% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 4 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Boston on average per day?
As of April 2025, there are 2 flights per day flying from Chicago Midway Airport to Boston. The most common time of day flights depart is 12:00PM, with 35% of flights taking off in the afternoon.
How many flights depart from Chicago Midway Airport to Boston on average per week?
The number of flights available between Chicago Midway Airport and Boston is 15 per week as of April 2025. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.
When to book flights from Chicago Midway Airport to Boston
Cheap Chicago Midway Airport to Boston (MDW to BOS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Boston
How far is Chicago Midway to Boston Logan Intl by plane?
Chicago Midway and Boston Logan Intl are 854.8 mi apart from one another. Typically, this will take 2h 15m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Boston Logan Intl Airport?
Prices for flights from Chicago Midway Airport to Boston Logan Intl Airport were last updated today.
How many operators does momondo search for flights from Chicago Midway Airport to Boston Logan Intl Airport?
The number of operators available for flights from Chicago Midway Airport to Boston Logan Intl Airport is 4 as of April 2025.
How old do you have to be to fly from Chicago Midway Airport to Boston Logan Intl 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 Chicago Midway Airport to Boston Logan Intl Airport.
What documentation or ID do you need to fly to Boston Logan Intl Airport?
The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago Midway Airport to Boston?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Boston is Boeing 737-800, representing 17.91% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 16.12%, Embraer 175 at 14.55%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 9.27%.
What is the most popular airline from Chicago Midway Airport to Boston?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Boston is Southwest (82% of total bookings). The next most popular airlines are Delta (8%), Frontier (5%), and United Airlines (5%).
Best airlines flying from Chicago Midway Airport to Boston
Compare and see reviews for airlines that fly from Chicago Midway Airport to Boston with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $63 | Free Cancellation | Rating 8.0 7,916 reviews | |||
| PriceFrom $86 | Free Cancellation | Rating 6.0 3,281 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Chicago Midway Airport to Boston
Southwest flight deals from Chicago Midway Airport to Boston start from $157 round-trip. Over the 15 Southwest flights for this route in a normal week, average airfare is usually $292 round-trip - but some users have found much cheaper deals with momondo.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Boston?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Boston for you.
Can I find flights from Chicago to Boston with flexible booking policies on momondo?
momondo does allow users to show only those flights to Boston from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Boston?
Once you have performed a search for Chicago to Boston 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 Chicago to Boston right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Boston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.