Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $110
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Massachusetts departing on 12/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/29
6:30 am-2:54 pm
1 stop7h 24m
Boston Logan Intl
Mon 11/2
6:25 pm-11:57 pm
1 stop6h 32m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 11/13
8:15 pm-11:59 pm
Nonstop2h 44m
Boston Logan Intl
Tue 11/17
12:15 pm-6:30 pm
1 stop7h 15m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 11/13
1:00 pm-4:49 pm
Nonstop2h 49m
Boston Logan Intl
Sat 11/14
11:27 am-6:30 pm
1 stop8h 03m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 1/16
7:05 am-12:21 pm
1 stop4h 16m
Boston Logan Intl
Tue 1/19
8:50 am-1:09 pm
1 stop5h 19m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 12/5
8:52 am-2:32 pm
1 stop4h 40m
Boston Logan Intl
Tue 12/8
5:45 am-9:37 am
1 stop4h 52m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 11/14
5:30 am-1:42 pm
1 stop7h 12m
Boston Logan Intl
Mon 11/16
9:15 am-1:59 pm
1 stop5h 44m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 10/26
8:24 pm-12:08 am
Nonstop2h 44m
Boston Logan Intl
Fri 10/30
5:15 pm-7:29 pm
Nonstop3h 14m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/31
6:00 am-9:37 am
Nonstop2h 37m
Boston Logan Intl
Sat 10/31
7:23 pm-9:29 pm
Nonstop3h 06m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 10/23
6:10 am-2:29 pm
1 stop7h 19m
Boston Logan Intl
Mon 10/26
5:15 pm-7:29 pm
Nonstop3h 14m
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/24
12:00 pm-3:26 pm
Nonstop2h 26m
Boston Logan Intl
Fri 11/27
6:48 am-9:10 am
Nonstop3h 22m
See travel insights to Massachusetts from
How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Massachusetts
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 Massachusetts?
In general, January is the cheapest month to fly from Chicago O'Hare Intl Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $206. If you aren’t able to travel to Massachusetts during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $236.
What is the cheapest day to depart on your flight to Massachusetts?
According to our data, Saturday is the cheapest day to fly to Massachusetts from Chicago O'Hare Intl Airport. The lowest ticket price found for a Saturday departure recently was $263. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $341.
What is the cheapest time of day to depart on your flight to Massachusetts?
Our data shows that the cheapest Chicago O'Hare Intl Airport to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $255. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $326 on average. Flights to Massachusetts from Chicago O'Hare Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago O'Hare Intl to Massachusetts flight route?
Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - Massachusetts flight prices
How far in advance should I book a flight from Chicago O'Hare Intl Airport to Massachusetts?
You are more likely to see cheaper flights to Massachusetts from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $270 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago O'Hare Intl Airport for as low as $231 on momondo.
What cabin class options are available on Chicago O'Hare Intl Airport to Massachusetts flights?
There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago O'Hare Intl to Massachusetts?
Delta and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Massachusetts
What airlines fly to Massachusetts?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 4 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago O'Hare Intl Airport to Massachusetts on average per day?
The number of flights available between Chicago O'Hare Intl Airport and Massachusetts is 56 per day as of October 2026. The most frequent departure time is 9:00AM, with 48% of daily flights leaving at noon.
How many flights depart from Chicago O'Hare Intl Airport to Massachusetts on average per week?
As of October 2026, 393 flights take off from Chicago O'Hare Intl Airport and land in Massachusetts each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.
Cheap Chicago O'Hare Intl Airport to Massachusetts flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Massachusetts
Frequently asked questions about flying from Chicago O'Hare Intl Airport to Massachusetts
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Massachusetts?
Prices for flights from Chicago O'Hare Intl Airport to Massachusetts are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Massachusetts?
There are 4 operators available for flights from Chicago O'Hare Intl Airport to Massachusetts as of October 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Massachusetts?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents you'll need for your trip to Massachusetts 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 Massachusetts. 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 Chicago O'Hare Intl Airport to Massachusetts?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago O'Hare Intl Airport to Massachusetts is Boeing 737-800 (19.04% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (11.56%), Airbus A220-300 (11.23%), and Boeing 737-900 (10.54%).
Best airlines flying from Chicago O'Hare Intl Airport to Massachusetts
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Massachusetts with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $86 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $92 | Free Cancellation | Rating 7.8 8,645 reviews | |||
| PriceFrom $135 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $141 | Free Cancellation | Rating 7.0 12,146 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Massachusetts?
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 Massachusetts from Chicago.
Can I find flights from Chicago to Massachusetts with flexible booking policies on momondo?
momondo does allow users to show only those flights to Massachusetts from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Massachusetts?
momondo provides multiple filters to help you find the best flight to Massachusetts from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?
Price alerts on flights to Massachusetts from Chicago 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.