ORD - BOS

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

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Everything you should know

Cheapest round-trip
$176
Typical prices: $178-$302
Frontier
Sun 9/2Wed 9/5
ORD - BOS • 1 stop
Cheapest non-stop
$203
Typical prices: $178-$302
JetBlue
Tue 10/2Sun 10/7
ORD - BOS • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and others. Average duration is 2h 36m.
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $170 (round-trip)
Shortest trip • 5h 16m (one-way)
Insights
Insights
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Booking Insights
Expert advice
Flight Deals

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

 
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, Sep 2 - Sat, Sep 5
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
$176Frontier
Wed, Sep 9 - Sat, Sep 12
Frontier Logo
3:50 pm - 10:22 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
17h 32m1 stop Orlando
Frontier Logo
12:54 pm - 6:23 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 29m1 stop Atlanta Hartsfield-Jackson
$183Frontier
Fri, Oct 2 - Wed, Oct 7
JetBlue Logo
6:30 am - 2:40 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 10m1 stop New York John F Kennedy Intl
JetBlue Logo
6:55 am - 8:46 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
$195JetBlue
Fri, Oct 2 - Wed, Oct 7
JetBlue Logo
6:30 am - 2:40 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 10m1 stop New York John F Kennedy Intl
JetBlue Logo
6:55 am - 11:47 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 52m1 stop New York John F Kennedy Intl
$197JetBlue
Tue, Jan 26 - Tue, Feb 23
United Airlines Logo
4:10 pm - 7:38 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
United Airlines Logo
6:33 pm - 8:25 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
$255United Airlines
Thu, Oct 1 - Sun, Oct 4
United Airlines Logo
9:24 pm - 12:54 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
United Airlines Logo
6:00 am - 7:59 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
$255United Airlines
Sat, Sep 26 - Sun, Sep 27
American Airlines Logo
6:50 am - 10:29 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
American Airlines Logo
6:00 am - 8:10 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 10mnonstop
$255American Airlines
Sun, Sep 6 - Mon, Sep 7
American Airlines Logo
7:15 pm - 10:50 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
American Airlines Logo
6:14 am - 8:20 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 06mnonstop
$255American Airlines
Mon, Nov 16 - Fri, Nov 20
Delta Logo
10:35 am - 1:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 24mnonstop
Delta Logo
7:30 am - 9:35 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
$255Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
7:30 pm - 11:09 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 39mnonstop
Delta Logo
8:50 pm - 10:32 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 42mnonstop
$255Delta
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Boston flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago O'Hare Intl Airport to Boston with more confidence.

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

Round-trip flights from Chicago O'Hare Intl Airport to Boston start at $176. Prices are below average for this route right now, with typical round-trip fares ranging from $178 to $302. The lowest price found in the past 5 days was $176 on Frontier.

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

Wednesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Boston, it is 9% cheaper than the average day. Monday is the most expensive day with flight prices 16% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • January is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston at $188 round-trip.
  • December ($249) and June ($247) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 32% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago O'Hare Intl Airport to Boston the cheapest?

Flights from Chicago O'Hare Intl Airport to Boston are cheapest 5 weeks before departure. Booking in this window typically costs about 26% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

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

 
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.

Key details for Chicago O'Hare Intl Airport to Boston flights

Low season

January

Cheapest flight

$94
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Intl 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

Your Chicago O'Hare Intl Airport to Boston flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • Which airlines offer extra legroom and free seat selection on Chicago O'Hare Intl Airport to Boston flights?

    Among airlines operating Chicago O'Hare Intl Airport to Boston flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Delta: offers extra legroom; offers free seat selection
    • JetBlue: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago O'Hare Intl Airport to Boston?

    4 airlines operate flights between Chicago O'Hare Intl Airport and Boston. The airlines offering nonstop flights on this route include:
    • American Airlines
    • United Airlines
    • Delta
    • JetBlue

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Boston?

    Flights from Chicago O'Hare Intl Airport to Boston usually depart from Chicago O'Hare Intl (ORD) and arrive at Boston Logan Intl (BOS).

  • Which airlines include bags at no extra cost on Chicago O'Hare Intl Airport to Boston flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Delta: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Boston?

    Four cabin classes are available on flights from Chicago O'Hare Intl Airport to Boston:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How much can I save by taking a layover when flying from Chicago O'Hare Intl Airport to Boston?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $170 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $230 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago O'Hare Intl Airport to Boston?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago O'Hare Intl Airport to Boston?

    The Boeing 737-800 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 9 variants.

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Boston pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Boston most commonly connect through:

    • Nashville Intl (BNA) - 25% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 13% of one-stop connections
    • Baltimore/Washington (BWI) - 13% of one-stop connections
    • Denver Intl (DEN) - 13% of one-stop connections

    Nashville Intl (BNA) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Boston?

    Yes. Being flexible with your travel dates can save you up to 22% on the Chicago O'Hare Intl Airport to Boston route. Wednesday is the cheapest departure day at $211 round-trip on average, while Monday is the most expensive at $269, a difference of $58. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Chicago O'Hare Intl Airport to Boston?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago O'Hare Intl Airport to Boston route, 25% of flights were delayed in the past 3 months, with delays averaging 2 hours 36 minutes.

  • How are flight departures from Chicago O'Hare Intl Airport to Boston spread across the day?

    Morning is the busiest departure period on Chicago O'Hare Intl Airport to Boston flights, with 48% of flights leaving in that window. Evening departures account for 24%, night flights for 20%, and afternoon flights for 8%.

  • What popular places can I visit in Boston?

    Some of the most popular sights in Boston are Fenway Park, TD Garden and South Station. These are among the most viewed places in Boston on KAYAK.

  • How long is a flight from Chicago O'Hare Intl Airport to Boston?

    A nonstop flight from Chicago O'Hare Intl Airport to Boston takes 2h 36m, covering 864 miles.

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to Boston?

    These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to Boston:

    • Earliest: departs at 6:00 am and lands at 8:36 am
    • Latest: departs at 9:45 pm and lands at 12:21 am.

    The flight takes about 2h 36m.

  • How expensive are last-minute Chicago O'Hare Intl Airport to Boston flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 19% above the route average of $230. Book 5 weeks before departure for the lowest fares.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Boston?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Chicago O'Hare Intl Airport to Boston changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $176 to $1,011. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Chicago O'Hare Intl Airport to Boston looking right now?

    One-way fares from Chicago O'Hare Intl Airport to Boston are currently lower than usual. Average one-way flight prices are about $116, which is 31% below the typical average for this route.

  • How does Delta’s on-time performance compare to other airlines on Chicago O'Hare Intl Airport to Boston flights?

    Delta is slightly above the route average for timely arrivals, while JetBlue has a lower on-time arrival rate. On-time arrival rates on Chicago O'Hare Intl Airport to Boston flights are:

    • Delta: 80% on time
    • JetBlue: 79% on time
    • United Airlines: 75% on time

    Overall, flights on this route are on time 75% of the time on average.

  • How do delay rates compare for morning and evening flights from Chicago O'Hare Intl Airport to Boston?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to Boston?

    Flying via Philadelphia (PHL) gives the shortest average 1-stop total travel time at 5h 16m, compared with 5h 20m via Baltimore/Washington (BWI) and 5h 39m via New York John F Kennedy Intl (JFK).

  • What is the time difference between Chicago O'Hare Intl Airport and Boston?

    Boston is 1 hour ahead of Chicago O'Hare Intl Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Boston Logan Intl Airport (BOS)?

    Boston Logan Intl Airport (BOS) hosts 5 major car rental companies, with daily rates starting from around $23 for economy cars. Top options include:
    · Dollar
    · Hertz
    · Budget
    · Thrifty
    · Sixt

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Boston flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Boston range from $178 to $302, with an average of $230 over the past 12 months. Anything below $178 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago O'Hare Intl Airport to Boston flights?

    Three airlines offer in-flight Wi-Fi on Chicago O'Hare Intl Airport to Boston flights:

    • • American Airlines
    • • Delta
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Chicago O'Hare Intl Airport to Boston flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Monday. On this route, Wednesday flights average $211 - about $58 less than Monday (22% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 5 weeks before you fly. On this route, that window historically saves about 26% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Boston trip for January. Fares historically average $188 round-trip in that month - typically $61 less than the most expensive month, which is December (based on the last 12 months).
  • If arriving on time is high on your priority list, Delta is the strongest pick on this route. 80% of Delta flights from Chicago O'Hare Intl Airport to Boston arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 75%. When flights on this route do arrive late, the average delay is 2 hours 36 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $170 round-trip on this route - about $60 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Boston Logan Intl Airport.
    - Courtyard by Marriott Boston Logan Airport
    - Embassy Suites by Hilton Boston at Logan Airport
    - Hyatt Regency Boston Harbor
  • 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?

 
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

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

Information on your arrival and departure airports