Cheap flights from Boston to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport departing on 4/29. 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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JetBlue flights from Boston to Chicago O'Hare Intl Airport
Our best JetBlue deals on Boston to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines flights from Boston to Chicago O'Hare Intl Airport
Our best Spirit Airlines deals on Boston to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Boston to Chicago O'Hare Intl 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 O'Hare Intl Airport?
The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Boston averaging around $207.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $321. This is often the case because there is less demand to fly during this day of the week. 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 $430.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $253 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $371. 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 O'Hare Intl flight route?
Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Boston when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $249 when searching 23 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Boston for as low as $176 on momondo.
What cabin class options are available on Boston Logan Intl to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago O'Hare 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 Boston Logan Intl to Chicago O'Hare Intl?
JetBlue, American Airlines, and United Airlines are the most popular carriers operating from Boston Logan Intl to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Boston according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Boston to Chicago O'Hare Intl Airport on average per day?
The number of flights available between Boston and Chicago O'Hare Intl Airport is 47 per day as of March 2025. The most frequent departure time is 10:00AM, with 46% of daily flights leaving at noon.
How many flights depart from Boston to Chicago O'Hare Intl Airport on average per week?
As of March 2025, there are 331 flights per week flying from Boston to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.
When to book flights from Boston to Chicago O'Hare Intl Airport
Cheap Boston to Chicago O'Hare Intl Airport (BOS to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago O'Hare Intl Airport
How far is Boston Logan Intl to Chicago O'Hare Intl by plane?
A flight from Boston Logan Intl to Chicago O'Hare Intl will travel around 861.0 mi. 2h 52m is a normal flight duration for this route.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport are updated daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
There are 6 operators available for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport as of March 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago O'Hare 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 Boston Logan Intl Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The required travel and health documents for your Chicago O'Hare 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 Chicago O'Hare 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 Boston to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Boston and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737-800, making up 23.82% of the total bookings. Other popular models include Embraer 175 with 17.28%, Boeing 737 MAX 8 with 11.40%, and Boeing 737-900 with 7.89%.
What is the most popular airline from Boston to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Boston to Chicago O'Hare Intl Airport is American Airlines, representing 34% of all bookings. The subsequent popular airlines are United Airlines at 29%, Delta at 18%, and JetBlue at 9%.
Best airlines flying from Boston to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Boston to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $39 | Free Cancellation | Rating 6.3 7,878 reviews | |||
| PriceFrom $84 | Free Cancellation | Rating 7.3 2,924 reviews | |||
| PriceFrom $95 | Free Cancellation | Rating 8.0 7,888 reviews | |||
| PriceFrom $99 | Free Cancellation | Rating 6.0 3,273 reviews | |||
| PriceFrom $143 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $155 | Free Cancellation | Rating 7.4 8,603 reviews |
Delta Flights From Boston to Chicago O'Hare Intl Airport
Delta is one of the most popular airlines flying from Boston to Chicago O'Hare Intl Airport, operating 16 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from $95 round-trip, up to an average price of $247. Our users have rated Delta at 8.0/10.
United Airlines Flights From Boston to Chicago O'Hare Intl Airport
United Airlines (7.4/10 from 8,603 reviews) operates around 42 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average United Airlines airfare for this route is around $296, with deals from around $155 rare but found on momondo. Referenced prices are for round-trip Boston to Chicago O'Hare Intl Airport flight searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Boston to Chicago?
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 Boston to Chicago for you.
Can I find flights from Boston to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Boston to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Boston to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Boston to Chicago.
I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Boston to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.