Cheap flights from O'Hare Intl (ORD) to Boston (BOS) from $49

This is the cheapest one-way flight price, found on 5/24. Prices may vary by date and flight preferences.
ORD — BOS
May 30 — Jun 61
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How to find the cheapest flight from O'Hare Intl (ORD) to Boston (BOS)

All the information you need to plan the best ORD to BOS flight in 2023: compare O'Hare Intl to Boston flight prices with the expected peak season, weather and rainfall in Boston.

Popular in

July

Cheapest in

February

Round-trip from

$158

One-way from

$89
High demand for flights, 21% potential price rise
Best time to find cheap flights, 34% potential price drop
From Chicago O'Hare Intl to Boston Logan Intl
One-way flight from Chicago O'Hare Intl to Boston Logan Intl

ORD - BOS

Price

$158 - $302

BOS

Temperature

30.2 - 73.4 °F

BOS

Rainfall

3.1 - 4 inches

Cheap flights from O'Hare Intl to Boston in May, June 2023

The best prices found for ORD to BOS flights for May, June
The lowest fares we've come across on flights traveling from Chicago to Boston in May and June 2023. For more flight deals, be sure to check back very soon.

O'Hare Intl to Boston 2023 flight deals

Cheap flights to Boston from O'Hare Intl found for this year
The lowest fares we've come across on flights traveling from Chicago to Boston in May and June 2023. For more flight deals, be sure to check back very soon.

Cheap United Airlines flights from O'Hare Intl to Boston

Check out some of the cheapest United Airlines flights we've come across from Chicago to Boston. It's recommended that users confirm their flight details before booking.
  • If you’re traveling from Chicago O'Hare Intl Airport to Boston, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $366.00 RT. This price is typically 38% more expensive than other airlines that offer Chicago O'Hare Intl Airport to Boston flights. When booking this route, the cheapest RT price found was $244. The most popular departure airport in Chicago O'Hare Intl Airport when flying to Boston is Chicago O'Hare Intl Airport. The most popular airport to fly into when visiting Boston is Boston Logan Intl Airport. When flying from Chicago O'Hare Intl Airport to Boston, United Airlines flights are 8% more popular than any other airline flying that same route.

Cheap Spirit Airlines flights from O'Hare Intl to Boston

To aid your search, here are some of the cheapest Spirit Airlines flights we've found from Chicago to Boston. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
  • If you’re traveling from Chicago O'Hare Intl Airport to Boston, one of the more common airlines traveling that route is Spirit Airlines. Chicago O'Hare Intl Airport to Boston flights are typically 70% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $227.81 RT. The cheapest Spirit Airlines flight found for this route was $82. When traveling from Chicago O'Hare Intl Airport to Boston on Spirit Airlines, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is Boston Logan Intl Airport. When flying from Chicago O'Hare Intl Airport to Boston, Spirit Airlines flights are 7% more popular than any other airline flying that same route.

Non-stop flights to Boston from O'Hare Intl

Save time with O'Hare Intl to Boston direct flight deals
For a shorter flight, select one of these non-stop flights from Chicago to Boston. Users seeking other options on flights from Chicago to Boston should update the search form at the top of the page.

Last minute flights from O'Hare Intl to Boston

Late deals on return flights to Boston from O'Hare Intl, departing today and this week
Book one of these great deals on flights from Chicago to Boston. Users should examine the flight details to ensure there are no surprises.

One-way flights to Boston from O'Hare Intl

The cheapest one-way flights from O'Hare Intl to Boston
Take a look at some of the one-way flights we've detected from Chicago to Boston. For those needing a return trip from Chicago, there is a search form available above.

Find flights from O'Hare Intl to Boston within your budget

Use the slider to find flights from O'Hare Intl to Boston that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$98 - $191

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/6

Nonstop2h 24m

Boston Logan Intl

Wed 9/13

Nonstop2h 59m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/23

1 stop7h 38m

Boston Logan Intl

Wed 8/30

Nonstop3h 06m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/23

1 stop7h 38m

Boston Logan Intl

Tue 8/29

1 stop4h 29m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/6

1 stop7h 37m

Boston Logan Intl

Wed 9/13

1 stop8h 35m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/6

1 stop4h 58m

Boston Logan Intl

Wed 9/13

Nonstop2h 52m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/11

1 stop16h 54m

Boston Logan Intl

Wed 7/19

1 stop11h 38m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/11

Nonstop2h 31m

Boston Logan Intl

Wed 7/12

Nonstop2h 48m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/11

1 stop9h 46m

Boston Logan Intl

Tue 7/18

Nonstop3h 06m

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/7

1 stop4h 44m

Boston Logan Intl

Mon 9/11

Nonstop2h 54m

Flights are sorted by cheapest first

Deals found on 5/24

Reviews of Airlines Servicing Boston

Read reviews from past customers who have flown United Airlines, Spirit Airlines and Undisclosed Carrier from Chicago to Boston. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

Delta
8.0
Very good
2,342 reviews
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

United Airlines
7.6
Good
1,488 reviews
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

JetBlue
7.5
Good
593 reviews
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

American Airlines
7.4
Good
2,147 reviews
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

Spirit Airlines
6.6
Okay
1,011 reviews
Delta
8.0
Very good
2,342 reviews

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 10

Delta cancelled our chosen flight in the middle of the night prior to our departure and automatically rescheduled us for a later, longer flight I never would have chosen. I know for a fact the flight was full because I had chosen (and paid for) our seating assignments at the time I purchased the tickets. Thus we had a much more arduous experience and had trouble arranging for a driver pick up at the Tucson airport. Our final destination was 1 hour away from the airport, in Green Valley, and this was not acceptable to us, even though we had no other option. We finally arrived at our accommodations at midnight. Very late for us. I also had to pay for "new seating fees" to complete our morning pre-flight check in for this new flight because there was no way to bypass the option online. Thus, I want to be reimbursed for the double fees fees I was charged. Not happy. Not happy at all with Delta...

Related info for your journey

Useful info, stats and facts about O'Hare Intl to Boston flights.

Top 6 airlines flying from O'Hare Intl to Boston

The chart below displays the airlines Cheapflights users traveling from O'Hare Intl to Boston choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
JetBlueCheapest$79Average$215FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
DeltaCheapest$82Average$228FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$90Average$258FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$109Average$255FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Spirit AirlinesCheapest$117Average$197FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
Alaska AirlinesCheapest$244Average$366FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from O'Hare Intl to Boston

See what time of day planes typically take off from O'Hare Intl to Boston
8%of flight departuresEarly morningMidnight to 6 am
37%of flight departuresMorning6 am to noon
40%of flight departuresAfternoonNoon to 6 pm
15%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from O'Hare Intl to Boston

See how many times per day planes take to the skies headed from O'Hare Intl to Boston
Sunday57daily flights
Monday61daily flights
Tuesday53daily flights
Wednesday53daily flights
Thursday56daily flights
Friday54daily flights
Saturday42daily flights