Cheap flights from Massachusetts to Chicago from $106
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago departing on 10/27. 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
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 11/16
9:15 am-1:59 pm
1 stop5h 44m
Chicago O'Hare Intl
Thu 11/19
10:35 am-1:59 pm
Nonstop2h 24m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 11/14
7:55 pm-9:51 pm
Nonstop2h 56m
Chicago O'Hare Intl
Tue 11/17
8:45 am-2:21 pm
1 stop4h 36m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/27
9:12 am-11:15 am
Nonstop3h 03m
Chicago O'Hare Intl
Sat 10/31
6:59 am-12:26 pm
1 stop4h 27m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 10/28
4:38 pm-6:42 pm
Nonstop3h 04m
Chicago O'Hare Intl
Sat 10/31
8:50 am-2:32 pm
1 stop4h 42m
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 12/7
5:55 pm-7:40 pm
Nonstop2h 45m
Chicago Midway
Sat 12/12
6:35 am-2:20 pm
1 stop6h 45m
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 12/7
5:45 pm-10:40 pm
1 stop5h 55m
Chicago Midway
Thu 12/10
8:30 am-12:00 pm
Nonstop2h 30m
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 12/7
11:08 am-8:42 pm
1 stop10h 34m
Chicago Midway
Thu 12/10
9:37 am-3:54 pm
1 stop5h 17m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 12/3
11:34 am-9:40 pm
1 stop11h 06m
Chicago O'Hare Intl
Thu 12/10
10:37 pm-10:39 am
1 stop11h 02m
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Mon 10/26
5:16 pm-10:30 pm
1 stop6h 14m
Chicago O'Hare Intl
Wed 10/28
6:29 am-4:49 pm
1 stop9h 20m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 11/24
5:39 am-8:00 am
Nonstop3h 21m
Chicago O'Hare Intl
Fri 11/27
12:00 pm-3:26 pm
Nonstop2h 26m
See travel insights to Chicago from
How to get the cheapest flight ticket from Massachusetts to Chicago
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 Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $197. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Massachusetts to Chicago during February average around $217.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $330. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Chicago for around $421.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $296. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $363.
What is the cheapest Massachusetts to Chicago flight route?
Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Chicago flight prices
How far in advance should I book a flight from Massachusetts to Chicago?
You are more likely to see cheaper flights to Chicago from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $268 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Massachusetts for as low as $225 on momondo.
What cabin class options are available on Massachusetts to Chicago flights?
There are 4 cabin classes available to choose from on Massachusetts to Chicago 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 Massachusetts to Chicago?
Delta, Southwest, and United Airlines are the most popular carriers operating from Massachusetts to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Massachusetts according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Massachusetts to Chicago on average per day?
57 flights are operational daily from Massachusetts to Chicago as of October 2026. The most popular departure time for this route is 7:00AM, with 41% of flights per day taking off in the afternoon.
How many flights depart from Massachusetts to Chicago on average per week?
404 flights are operational weekly from Massachusetts to Chicago as of October 2026. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.
Cheap Massachusetts to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago
Frequently asked questions about flying from Massachusetts to Chicago
When did momondo last update prices for flights from Massachusetts to Chicago?
Prices for flights from Massachusetts to Chicago are updated daily.
How many operators does momondo search for flights from Massachusetts to Chicago?
There are 5 operators available for flights from Massachusetts to Chicago as of October 2026.
How old do you have to be to fly from Massachusetts to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Massachusetts to Chicago?
Based on momondo bookings for flights between Massachusetts and Chicago, the leading plane model is Boeing 737-800, making up 18.59% of the total bookings. Other popular models include Boeing 737 MAX 8 with 11.54%, Airbus A321neo with 11.51%, and Boeing 737 MAX 9 with 10.16%.
Best airlines flying from Massachusetts to Chicago
Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $73 | Free Cancellation | Rating 7.1 3,049 reviews | |||
| PriceFrom $88 | Free Cancellation | Rating 7.8 8,645 reviews | |||
| PriceFrom $135 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $147 | Free Cancellation | Rating 7.9 4,222 reviews | |||
| PriceFrom $147 | Free Cancellation | Rating 7.0 12,145 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Massachusetts to Chicago?
It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Massachusetts to Chicago?
Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.