BOS to CHI (Boston to Chicago) Flights

Last Minute Flights from BOS to CHI

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
BOSRockfordMarch 20 to April 3$196
*Prices include taxes and fees

Cheapest BOS to CHI Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
BOSRockfordApril 14 to April 16$139
BOSChicagoApril 13 to April 15$157
BOSChicagoApril 13 to April 15$177
BOSChicagoApril 13 to April 15$177
BOSChicagoApril 15 to April 18$180
*Prices include taxes and fees
BOS to CHI Flight Details
Origin airport
Logan Intl.
Origin airport IATA code
BOS
Destination airport
Greater Rockford
Destination airport IATA code
RFD
Distance
922 mi

Frequently asked questions

How many flights are there from BOS to Chicago, IL (CHI-All Airports)?
Approximately 22 each day. If you're in a hurry to get to Illinois, see if you can grab a good last-minute deal from Boston, MA (BOS-Logan Intl.) to Chicago, IL (CHI-All Airports) and then secure it right away!
How many morning flights are there from BOS to Chicago, IL (CHI-All Airports)?
Those who love to rise early can choose from 69 morning flights from BOS to Chicago, IL (CHI-All Airports) per week.

  • United Airlines (UA) has 21 weekly flights that leave the gate before midday. The first departure is 6:01AM.
  • American Airlines (AA) is an alternative option. It lists 16 flights before noon each week, the earliest of which leaves at 5:25AM.

How many afternoon flights are there from BOS to Chicago, IL (CHI-All Airports)?
With 89 afternoon and evening flights from BOS to Chicago, IL (CHI-All Airports) per week, you can forget about sleep-deprived starts.

  • American Airlines (AA) has 26 weekly services that jet off after midday. The earliest departure is 4:05PM.
  • United Airlines (UA) offers 24 afternoon and evening flights each week. The first departs at 4:42PM.
  • Alternatively, cruise at altitude with Delta Air Lines (DL). This carrier has 20 flights per week after midday, with the earliest departure at 12:55AM.

What is the earliest departure time out of Boston to Illinois?
Head out from BOS at 5:25AM and land at Chicago, IL (CHI-All Airports) at 8:21AM. This flight is the earliest you can catch on this route.
What is the latest departure time out of Boston to Illinois?
Book a seat on the 9:55PM flight from BOS, touching down at 12:30AM at Chicago, IL (CHI-All Airports), and allow yourself time to deal with those last-minute vacation preparations. This is the latest flight you can take on this route.
What is the average price from Boston to Illinois?
On average, the lowest price for a round-trip airfare from BOS to Chicago, IL (CHI-All Airports) is $139. Pick up your own great bargain by locking in your seats soon. 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 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 simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from BOS to CHI, we’ve got you covered here at Flights.com.

We present you with some of the most affordable 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.

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