Cheap flights from Boston to Chicago from ₹ 5,400
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 18/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customie your resultsTrusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Boston to Chicago
Cheap return flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
American Airlines flights from Boston to Chicago O'Hare Intl Airport
Our best American Airlines deals on Boston to Chicago O'Hare Intl Airport flight tickets
JetBlue flights from Boston to Chicago O'Hare Intl Airport
Our best JetBlue deals on Boston to Chicago O'Hare Intl Airport flight tickets
See travel insights to Chicago from
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 cheapest month to fly to Chicago O'Hare Intl Airport from Boston is in September. Flight prices, which tend to average around ₹ 16,115, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago O'Hare Intl Airport in September, then you should wait until August to fly from Boston, when ticket prices are also cheap, with an average price of ₹ 17,058.
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 Thursday when prices can be found for as low as ₹ 12,627. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around ₹ 28,379. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago O'Hare Intl Airport.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
In the afternoon is the cheapest time of day to fly from Boston to Chicago O'Hare Intl Airport when you can find flight prices for as low as ₹ 21,934. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are ₹ 28,379 on average. Flights to Chicago O'Hare Intl Airport from Boston in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.
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 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around ₹ 20,695 when searching 5 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 ₹ 17,916 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.
Can stopping save me money on Boston to Chicago O'Hare Intl Airport flights?
No. A direct flight is the cheapest option for a flight between Boston to Chicago O'Hare Intl Airport.
How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?
As of June 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 31% cheaper when compared to flights at the same time last year.
How many flights depart from Boston to Chicago O'Hare Intl Airport on average per day?
As of June 2025, there are 70 flights per day flying from Boston to Chicago O'Hare Intl Airport. The most common time of day flights depart is 06:00, with 43% of flights taking off in the afternoon.
How many flights depart from Boston to Chicago O'Hare Intl Airport on average per week?
493 flights are operational weekly from Boston to Chicago O'Hare Intl Airport as of June 2025. The most popular departure day for this route is Mon, with 16% of flights per week 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?
Boston Logan Intl and Chicago O'Hare Intl are 1385.7 km apart from one another. A reasonable flight in good conditions will take 2h 48m.
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 refresh daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
There are 2 operators available for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport as of June 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 travel and health documents you'll need for your trip to Chicago O'Hare Intl 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 O'Hare Intl 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 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 25.74% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.72%, Embraer 175 with 11.00%, and Boeing 737-900 with 10.79%.
What is the most popular airline from Boston to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Chicago O'Hare Intl Airport is American Airlines (69% of total bookings). The next most popular airline is Delta (31%).
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 ₹ 13,453 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom ₹ 20,323 | Free Cancellation | Rating 7.2 10,000 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 20 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from ₹ 157 round-trip, up to an average price of ₹ 229. Our users have rated Delta at 8.0/10.
American Airlines Flights From Boston to Chicago O'Hare Intl Airport
American Airlines (7.2/10 from 10,000 reviews) operates around 62 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around ₹ 331, with deals from around ₹ 237 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.
Travelling 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?
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?
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?
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.