ORD - BOS

$94 Find Cheap Flights from Chicago O'Hare Airport to Boston - Compare and Save

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 7/11. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$176
Typical prices: $181-$333
JetBlue
Sat 8/8Sat 8/15
ORD - BOS • 1 stop
Cheapest non-stop
$178
Typical prices: $137-$278
Delta
Sat 9/5Fri 9/11
ORD - BOS • Non-stop
Top airlines
Cheapest • from $176 (round-trip)
Best reviews • 7.9 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 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
+1
+1
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+1
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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

Sat, Aug 8 - Sat, Aug 15
JetBlue Logo
6:00 am - 2:24 pm
ORD
-
BOS
7h 24m
1 stop
JetBlue Logo
4:43 pm - 9:58 pm
BOS
-
ORD
6h 15m
1 stop
$176JetBlue
Thu, Aug 20 - Fri, Aug 21
JetBlue Logo
6:00 am - 2:43 pm
ORD
-
BOS
7h 43m
1 stop
JetBlue Logo
8:41 am - 4:17 pm
BOS
-
ORD
8h 36m
1 stop
$177JetBlue
Sat, Sep 5 - Fri, Sep 11
Delta Logo
7:30 am - 10:59 am
ORD
-
BOS
2h 29mnonstop
Delta Logo
7:30 am - 9:24 am
BOS
-
ORD
2h 54mnonstop
$178Delta
Fri, Jul 10 - Wed, Jul 15
Delta Logo
7:25 pm - 11:00 pm
ORD
-
BOS
2h 35mnonstop
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
$179Delta
Tue, Aug 25 - Wed, Aug 26
JetBlue Logo
6:00 am - 2:43 pm
ORD
-
BOS
7h 43m
1 stop
JetBlue Logo
8:15 am - 10:11 am
BOS
-
ORD
2h 56mnonstop
$180JetBlue
Sun, Sep 6 - Wed, Sep 16
Delta Logo
10:30 am - 1:59 pm
ORD
-
BOS
2h 29mnonstop
Delta Logo
4:30 pm - 6:28 pm
BOS
-
ORD
2h 58mnonstop
$181Delta
Sat, Aug 29 - Fri, Sep 4
Delta Logo
10:30 am - 1:59 pm
ORD
-
BOS
2h 29mnonstop
Delta Logo
8:50 pm - 10:44 pm
BOS
-
ORD
2h 54mnonstop
$182Delta
Tue, Jul 21 - Fri, Jul 24
Delta Logo
6:59 am - 10:30 am
ORD
-
BOS
2h 31mnonstop
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
$183Delta
Mon, Jul 27 - Tue, Jul 28
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
United Airlines Logo
7:27 pm - 11:31 pm
BOS
-
ORD
5h 04m
1 stop
$184United Airlines
Thu, Aug 13 - Mon, Aug 17
JetBlue Logo
9:35 am - 5:07 pm
ORD
-
BOS
6h 32m
1 stop
JetBlue Logo
8:41 am - 4:17 pm
BOS
-
ORD
8h 36m
1 stop
$185JetBlue
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 August.

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 Thursday 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 $204 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $286 and $267 respectively.

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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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.

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$94
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 1% 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

  • If you arrive at ORD airport early, what activities can you do to pass the time?

    There is a yoga room with mats where passengers can practice yoga, relax, and meditate as they wait for their flights. It is located on the mezzanine level of terminal 3. For those interested in the arts, there is a public art program with sculptures and paintings where you can browse art pieces before flying.

  • If you have an early morning flight, where can you spend the night in ORD?

    You can spend your night at the Hilton Chicago O'Hare airport hotel found within the airport grounds. It is located near terminals 1, 2, and 3, and you can walk from the airport to the hotel. The hotel has a fitness center, showers, restaurant, and elegant rooms.

  • Which family services are offered at ORD airport?

    ORD has a family lounge near gate F1 in terminal 2. The lounge has space where kids can play and stroller parking for passengers traveling with infants. Nursing rooms are also available in every terminal. They provide a clean and safe space for nursing parents to pump and breastfeed their babies. The rooms have changing tables, comfortable seats, and soft lighting, making them comfortable for lactating parents. Most restrooms in the terminals have changing stations for young children.

  • Are there child-friendly restaurants in ORD?

    Many restaurants offer high chairs and a children's menu. Some restaurants in ORD provide a fantastic view of the airplanes landing and taking off. These restaurants include Berghoff Café and the Food Court seating area found at terminal 1 near Gate C. Other restaurants like Tuscany at gate B18 in Terminal 1 have a view of the airplanes on the ground.

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was $94 for a one-way ticket and $176 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, Iberia, Finnair, and British Airways.

  • 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 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $242 and an overall rating of 7.8.

  • 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 $128 or less one-way and $217 or less round-trip.
  • If you are in Chicago O'Hare International Airport (ORD) and you lose items at the security lines or checkpoints, you can ask the security guards to help you locate them. If things get lost on the flight, contact your airline for assistance.
  • Passengers transiting throughinORD can stay connected while waiting for their flight. Every terminal has free Wi-Fi access. Changing stations are available in the seating areas to ensure your device's battery stays full.
  • If you want a place to pray and relax while waiting for your flight in ORD, there is a multi-faith chapel found at terminal 2 on the mezzanine level. Boston Logan International Airport (BOS) also has a place where you can pray. In the terminal C pre-security area, there is a chapel known as Our Lady of the Airways Chapel.
  • If you are traveling with your pet, ORD has six animal relief areas- four outdoor areas and two after airport security. ORD pet policy states that when traveling with a pet, they should be carried inside a crate or carrier at the airport.
  • If you want to travel from BOS to downtown Boston, you can take the MBTA into Boston. It is the most efficient and cost-effective way to reach the city from BOS. The air shuttle offers free shuttle services from the airport station to the rental car center, water taxi, and airline terminals.

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.
7.9
SouthwestOverall score based on 4243 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Long delay due to mechanical issues. They should have just swapped the plane and not make us wait while they figure it out. Disappointed

Flight was delayed but they still boarded us early knowing we were delayed. Were not able to move about the plane the majority of the flight.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

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

The tray table was broken and the food was terrible.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Advertised fruit trays with cheese, but only snacks handed out!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

I like flying first class, and United has a nice one

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

Good even though flight was delayed, the crew was prompt and efficient.

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 —

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.

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.

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.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

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

Information on your arrival and departure airports