ORD - BOS

$78 Find Cheap Flights from Chicago O'Hare Airport to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Boston departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$146
Typical prices: $303-$165
JetBlue
Wed 5/13Tue 5/19
ORD - BOS • Non-stop
Cheapest one-way
$78
Typical prices: $108-$260
Frontier
Fri 5/8
ORD - BOS • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue's Even More Space offers 7” extra legroom.
Expect 30-minute security lines at Chicago O'Hare.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $146 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Delta and others. Average duration is 2h 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $114 (round-trip)
Shortest trip • 4h 35m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from O'Hare Intl to Boston (ORD-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Boston

Wed, May 13 - Tue, May 19
JetBlue Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:47 pm - 8:53 pm
BOS
-
ORD
3h 06mnonstop
$146JetBlue
Tue, May 12 - Sat, May 16
Frontier Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Frontier Logo
12:01 pm - 7:51 pm
BOS
-
ORD
8h 50m
1 stop
$150Frontier
Sat, May 9 - Sun, May 10
JetBlue Logo
7:20 am - 10:46 am
ORD
-
BOS
2h 26mnonstop
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
$151JetBlue
Wed, May 13 - Sat, May 16
Frontier Logo
3:55 pm - 9:12 am
ORD
-
BOS
16h 17m
1 stop
Frontier Logo
10:07 am - 11:13 pm
BOS
-
ORD
14h 06m
1 stop
$153Frontier
Wed, May 13 - Sat, May 16
Multiple Airlines Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
Multiple Airlines Logo
12:01 pm - 7:51 pm
BOS
-
ORD
8h 50m
1 stop
$154Multiple Airlines
Sat, May 9 - Sun, May 10
JetBlue Logo
7:20 am - 10:46 am
ORD
-
BOS
2h 26mnonstop
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
$157JetBlue
Wed, May 13 - Tue, May 19
Multiple Airlines Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Multiple Airlines Logo
6:47 pm - 8:53 pm
BOS
-
ORD
3h 06mnonstop
$159Multiple Airlines
Tue, May 5 - Thu, May 7
Frontier Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Frontier Logo
9:31 am - 7:51 pm
BOS
-
ORD
11h 20m
1 stop
$160Frontier
Wed, May 13 - Sat, May 16
JetBlue Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:47 pm - 8:53 pm
BOS
-
ORD
3h 06mnonstop
$161JetBlue
Tue, May 12 - Tue, May 12
JetBlue Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:47 pm - 8:53 pm
BOS
-
ORD
3h 06mnonstop
$162JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Boston flights

Get data-powered insights and trends into flights from O'Hare Intl to Boston to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Boston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Boston departing in May.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Boston?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Boston clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Boston on a Wednesday and more expensive on a Monday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is September, where tickets cost $196 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $271 and $257 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Boston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $218 on average.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 2 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Expert advice

Expert advice for your flight from O'Hare Intl to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Delta and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonJanuary
Cheapest flight$78
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to Boston

When to book flights from O'Hare Intl to Boston

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Boston flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Boston?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was $78 for a one-way ticket and $146 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Boston?

    A passport is not required to fly from Chicago O'Hare Airport to Boston.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Boston?

    All the following airlines offer inflight Wi-Fi service on the Chicago O'Hare Airport to Boston flight route: American Airlines, JetBlue, Delta, Finnair, British Airways, and Iberia.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Boston?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Boston flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Boston?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Boston, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to Boston?

    There are nonstop flights from Chicago O'Hare Airport to Boston on a daily basis.

  • Which is the best airline for flights from Chicago to Boston, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Southwest and Delta. With an average price for the route of $206 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $234 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $121 or less one-way and $209 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Boston Logan Intl.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Boston Logan Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Direct returns

Boston Logan Intl to Chicago O'Hare Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Reviews of the top 5 airlines serving from O'Hare Intl to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4329 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

I almost missed my flight and they helped me out enormously

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Everything you need to know for your flight from O'Hare Intl to Boston

Information on your arrival and departure airports