BOS to ORD (Boston to Chicago) Flights

Last Minute Flights from BOS to ORD

Best airfare and ticket deals for BOS to ORD flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
BOSChicagoMay 18 to May 22$269
*Prices include taxes and fees

Cheapest BOS to ORD Flights

Best airfare and ticket deals for BOS to ORD flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
BOSChicagoAugust 22 to August 26$63
BOSChicagoJune 1 to June 4$110
BOSChicagoMay 30 to May 30$131
BOSChicagoAugust 20 to September 7$137
*Prices include taxes and fees
BOS to ORD Flight Details
Origin airport
Logan Intl.
Origin airport IATA code
BOS
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Distance
863 mi

Frequently asked questions

Which airlines with flights from BOS to Chicago, IL Airport (ORD-O'Hare Intl.) allow free cancellation due to COVID-19?
To find airlines that offer flexible COVID-19 related changes, take advantage of our helpful filter tool. Get started by typing in your dates, origin and destination details. Then, once the available flights appear, check the “No change fee” box under the “Flexible change policies” subheading to the left. Read through the carrier’s cancellation policies before reserving your BOS to Chicago, IL Airport (ORD-O’Hare Intl.) fare.
What airlines fly direct from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.)?
A selection of airlines operate nonstop flights between Boston, MA Airport (BOS-Logan Intl.) and ORD. Kick back and enjoy one stress-free journey from Boston to Chicago with any of the following:
  • United Airlines (UA)
  • American Airlines (AA)
  • Delta (DL)
  • JetBlue (B6)
How many flights are there from BOS to ORD?
About 20 per day. If you’re in a big rush to get to Chicago, see if you can score an incredible last-minute deal from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O’Hare Intl.) and then secure it fast!
How long does it take to fly from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.)?
The flight will take around 2 hours and 56 minutes from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O’Hare Intl.) — just long enough to get through a few chapters of your book!
What is the flight distance from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.)?
The short-haul flight from Boston to Chicago is just 860 miles (1400 km). Don’t settle in too much though — you’ll be coming into Chicago, IL Airport (ORD-O’Hare Intl.) not long after taking your seat.
How many morning flights are there from BOS to ORD?
Eager early birds can choose between 46 morning flights from BOS to ORD every week.
  • American Airlines (AA) offers 19 weekly services that leave before noon. The first departure is 5:15AM.
  • Or else, book a seat with United Airlines (UA) and take off as early as 6:00AM. This carrier lists 14 morning flights per week between BOS and ORD.
How many afternoon flights are there from BOS to ORD?
If the words “wake up early” just aren’t in your vocabulary, jump on one of the 72 weekly afternoon and evening flights from BOS to ORD.
  • United Airlines (UA) provides 27 weekly services that leave after midday. The earliest departure is 5:04PM.
  • Delta (DL) has 20 afternoon and evening flights a week. The first is at 12:25AM.
  • Otherwise you can fly out from 4:15PM onward with American Airlines (AA). This carrier operates 18 afternoon and evening flights every week.
What is the earliest departure time out of Boston to Chicago?
Head out from BOS at 5:00AM and come in for landing at ORD at 7:50AM. This flight is the earliest available on this route.
What is the latest departure time out of Boston to Chicago?
Book a seat on the 8:25PM flight out of BOS, arriving at 11:12PM at ORD, and give yourself time to attend to those last-minute vacation preparations. This is the latest flight you can catch on this route.
What is the average price from Boston to Chicago?
Round-trip tickets from BOS to ORD begin from around $63. Killer deals wait for no one, so have your credit card handy when you see a bargain. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Boston to Chicago Flight Schedule

CarrierFlightDepart BOSArrive ORDThu
5/16		Fri
5/17		Sat
5/18		Sun
5/19		Mon
5/20		Tue
5/21		Wed
5/22		Stops
AA226505:25 am07:21 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA56706:01 am07:54 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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B631106:10 am08:04 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL108806:25 am08:20 amCheck FareCheck Fare
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AA150907:10 am09:14 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA194408:00 am09:52 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA150208:50 am10:47 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA130609:40 am11:28 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL564210:15 am00:01 pmCheck FareCheck Fare
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AA145700:22 pm02:20 pmCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA173200:42 pm02:36 pmCheck FareCheck Fare
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AA30802:07 pm04:06 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL242702:10 pm04:04 pmCheck FareCheck Fare
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UA28903:15 pm05:08 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA371103:30 pm05:28 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL74204:43 pm06:45 pmCheck FareCheck Fare
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UA129805:02 pm06:55 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA148505:37 pm07:31 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA260906:31 pm08:25 pmCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL562507:59 pm09:46 pmCheck FareCheck Fare
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AA430110:00 am00:00 pm
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DL52100:50 pm02:49 pm
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DL561804:25 pm06:17 pm
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Boston to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Boston to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from BOS to ORD, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from Boston to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.