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Cheap Flights from Boston Logan International to Chicago

Compare Boston Logan International to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Boston Logan International to Chicago

Looking for a cheap last-minute deal or the best return flight from Boston Logan International to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.R 993 per passenger.Departing Mon, 20 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Boston Logan International on Mon, 20 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 993, select.
Chicago.R 1,005 per passenger.Departing Tue, 22 Jul.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Boston Logan International on Tue, 22 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,005, select.
Chicago.R 1,183 per passenger.Departing Tue, 30 Sep.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Tue, 30 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,183, select.
Chicago.R 1,183 per passenger.Departing Fri, 3 Oct.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Fri, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,183, select.
Chicago.R 1,204 per passenger.Departing Tue, 5 Aug.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Tue, 5 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,204, select.
Chicago.R 1,207 per passenger.Departing Sat, 21 Feb.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Boston Logan International on Sat, 21 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,207, select.
Chicago.R 1,207 per passenger.Departing Mon, 24 Nov.One-way flight with United.Outbound direct flight with United departs from Boston Logan International on Mon, 24 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,207, select.
Chicago.R 1,207 per passenger.Departing Wed, 9 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Boston Logan International on Wed, 9 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 1,207, select.

Find the cheapest month to fly from Boston Logan International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Boston Logan International to Chicago flights are currently cheapest in October.
Jul
from R 1,005
Aug
from R 1,204
Sep
from R 1,183
Oct
from R 993
Nov
from R 1,207
Dec
from R 1,215
Jan
from R 1,215
Feb
from R 1,207
Mar
from R 1,215
Apr
from R 1,215
May
from R 1,213
Jun
Find prices

Direct flights from Boston Logan International to Chicago

Alternative Boston Logan International to Chicago routes

Looking for the cheapest, fastest or easiest route from Boston Logan International to Chicago? You could fly into the following airports instead.

Boston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 993
Cheapest month to flyOctober
Average flight time2 hrs, 51 mins
Most popular airlineAmerican Airlines
Average flights per week763

Finding cheap flights from Boston Logan International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Boston Logan International to Chicago is R 2,236. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 50 minutes is the average flight time from Boston Logan International to Chicago.
American Airlines, Qatar Airways and Alaska Airlines fly direct from Boston Logan International to Chicago.
As of July 2025, there are 763 flights per week flying from Boston Logan International to Chicago.
The cheapest month to fly from Boston Logan International to Chicago is usually July.
If you're flying from Boston Logan International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from R 2,236.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Boston Logan International Airport to Chicago on Tuesday, 22 July 2025.
Yes – the average flight time is 2 hours and 50 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Spirit Airlines and jetBlue offer the cheapest flight tickets to Chicago.

Flying from Logan International Airport (BOS) to Chicago: what you need to know

  • Take a direct flight from Logan International Airport to Chicago and you'll be travelling for an average of 2 hours 30 minutes.

  • Logan International Airport is located in Boston. Based in the UTC-5 timezone, Chicago is one hour behind Boston.

  • The busiest route is from Logan International Airport (BOS) to O'Hare International Airport (ORD). Choose from 142 weekly services between these two airports. If you want to head off as soon as possible, the earliest flight from BOS to ORD is the 05:00 American Airlines service. If you prefer to travel later, the final departure is at 21:31 with United Airlines.

  • To avoid missing your BOS to Chicago flight, allow plenty of time for things like baggage drop and finding your gate. Turning up two hours before international departures and one hour before domestic flights is the general rule.

  • Planning to travel during a peak time like a bank holiday? Expect longer lines at security and check-in. Play it safe and arrive up to four hours before international flights and two hours before domestic departures.

  • Direct Logan International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) will be your arrival point.

  • Direct flights from Logan International Airport to Chicago are available from a range of airlines. Book your seat with any of these:

  • The journey from central Boston to BOS takes around 25 minutes by public transport. If you ride-share, drive or take a cab, you'll cover the 3 kilometres in 10 minutes or so, depending on traffic.

  • Have an early flight from Logan International Airport to Chicago? Avoid the hassle of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels close to BOS:

  • Of all flights departing from Logan International Airport, 73.94% land on time at their destination.

  • The address for BOS is One Harborside Drive.

How to find the cheapest flights from Logan International Airport (BOS) to Chicago

  • The lowest price we've found for a one-way Logan International Airport to Chicago flight is R 998. The cheapest price for a return flight is R 2,236. Bear in mind fares may change due to availability at the time of booking.

  • To secure cheap flights from BOS to Chicago, reserve your journey two months ahead of your departure.

  • The best month for finding cheap Logan International Airport to Chicago tickets is June. Use the 'Whole month' tool to compare prices, then select the dates that offer the biggest savings.

  • Never miss a deal on cheap flights from BOS to Chicago by setting up a Price Alert. You'll get an email or notification through the app when fares go down.

  • Pick your preferred departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Logan International Airport to Chicago by 'Fastest,' 'Best' or 'Cheapest.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes around 35 minutes to reach the centre driving.

  • Getting there on public transport typically takes 55 minutes.

  • Book a hotel close to ORD if you have a late flight from Logan International Airport to Chicago. Check in to one of these options and skip the long transfer:

  • Travel at your own pace with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.

  • To secure the lowest price, book your ride from O'Hare International Airport about four weeks ahead of your flight from BOS to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 19 kilometres from the centre of Chicago. After your flight from Logan International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • If you're catching public transport, it'll take about 45 minutes.

  • You'll find some great places to call home for the night near MDW. Kick back and get cosy after your BOS to Chicago flight at any of these perfectly located options:

  • Forget about public transport timetables or long cab queues. Pick up a Chicago Midway International Airport rental car and take your trip in whatever direction you choose. Compare availability and rates from Dollar, Hertz and Budget.

  • Lock in the best price by reserving your ride from MDW four weeks in advance. You can also expect to have a wider range of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Logan International Airport to Chicago and head for your hotel or start sightseeing right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to drive there.

  • The journey will take around 4 hours 15 minutes when travelling on public transport.

  • If you don't want to make your way to the centre, choose a hotel close to RFD. Get settled at one of these stays after your BOS to Chicago flight:

  • Begin your trip without stressing about how to get to your destination with a Chicago Rockford International Airport rental car. Book your wheels with trusted companies here like Budget, Alamo and National.

  • If you're looking for a certain type of vehicle, booking early gives you a better shot at getting exactly what you want. Book your ride from RFD a couple of weeks ahead of your flight from Logan International Airport to Chicago.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before securing your flight from Logan International Airport to Chicago. The city comes alive in peak season, but hotel rates are usually higher and major attractions can be busy. Go to Chicago in the low season if you want a quieter vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Logan International Airport to Chicago flight ticket then if you enjoy this type of weather.

  • For cooler conditions, search for a cheap ticket from BOS to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • Chicago has its own special appeal, but there are so many other corners of United States just waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're interested in discovering another great destination in United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key highlights.

Plan the rest of your trip from Boston to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.