Cheap Flights from Boston (BOS) to Chicago (ORD)

Return selected

origin

Enter the city you're flying from, or choose from the options below

Include nearby airports

selected

destination

. Enter your destination, or choose from the options below

Include nearby airports

selected

Travellers and cabin class, 1 Adult, Economy

Compare Boston Logan International to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

Book the best Chicago O'Hare International fare with no extra fees

Flight deals Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Boston Logan International to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Boston Logan International Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from $258. Find the lowest prices on one-way and return tickets right here.

Chicago.$237 per passenger.Departing Sat, 5 Dec, returning Sun, 6 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Boston Logan International on Sat, 5 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 6 Dec, arriving in Boston Logan International.Price includes taxes and charges.From $237, select.

Chicago.$258 per passenger.Departing Wed, 7 Oct, returning Sat, 10 Oct.Return flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Wed, 7 Oct, arriving in Chicago O'Hare International.Inbound direct flight with jetBlue departs from Chicago O'Hare International on Sat, 10 Oct, arriving in Boston Logan International.Price includes taxes and charges.From $258, select.

Chicago.$263 per passenger.Departing Tue, 20 Oct, returning Sun, 1 Nov.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Tue, 20 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Sun, 1 Nov, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Thu, 28 Jan, returning Thu, 28 Jan.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Thu, 28 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Thu, 28 Jan, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Sun, 31 Jan, returning Mon, 1 Feb.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Sun, 31 Jan, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Mon, 1 Feb, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Fri, 6 Nov, returning Sun, 15 Nov.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Fri, 6 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Sun, 15 Nov, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Sat, 12 Dec, returning Tue, 15 Dec.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Sat, 12 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Tue, 15 Dec, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Sat, 10 Oct, returning Sat, 9 Jan.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Sat, 10 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 9 Jan, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Mon, 1 Feb, returning Mon, 1 Feb.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Mon, 1 Feb, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Mon, 1 Feb, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$263 per passenger.Departing Tue, 29 Dec, returning Wed, 6 Jan.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Tue, 29 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 6 Jan, arriving in Boston Logan International.Price includes taxes and charges.From $263, select.

Chicago.$308 per passenger.Departing Fri, 27 Nov, returning Sun, 31 Jan.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Fri, 27 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 31 Jan, arriving in Boston Logan International.Price includes taxes and charges.From $308, select.

Chicago.$337 per passenger.Departing Thu, 19 Nov, returning Wed, 2 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Boston Logan International on Thu, 19 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 2 Dec, arriving in Boston Logan International.Price includes taxes and charges.From $337, select.

Chicago.$339 per passenger.Departing Thu, 19 Nov, returning Tue, 1 Dec.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Thu, 19 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Boston Logan International.Price includes taxes and charges.From $339, select.

Chicago.$374 per passenger.Departing Fri, 25 Sep, returning Sun, 22 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Boston Logan International on Fri, 25 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 22 Nov, arriving in Boston Logan International.Price includes taxes and charges.From $374, select.

Chicago.$380 per passenger.Departing Thu, 8 Apr, returning Sun, 11 Apr.Return flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Thu, 8 Apr, arriving in Chicago O'Hare International.Inbound direct flight with Delta departs from Chicago O'Hare International on Sun, 11 Apr, arriving in Boston Logan International.Price includes taxes and charges.From $380, select.

Chicago.$380 per passenger.Departing Thu, 1 Jul, returning Mon, 5 Jul.Return flight with United.Outbound direct flight with United departs from Boston Logan International on Thu, 1 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 5 Jul, arriving in Boston Logan International.Price includes taxes and charges.From $380, select.

Find the cheapest month to fly from Boston Logan International to Chicago O'Hare International

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 O'Hare International flights are currently cheapest in December.

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Direct flights from Boston Logan International to Chicago O'Hare International

Boston Logan International to Chicago O'Hare International: Alternative routes

Compare routes from Boston Logan International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Boston to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$237
Cheapest month to fly	December
Average flight time	3 hrs, 4 mins
Most popular airline	American Airlines
Average flights per week	643

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

How much are return flights from Boston Logan International to Chicago O'Hare International?

The best price we found for a return flight from Boston Logan International to Chicago O'Hare International is $237. 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.

How long does it take to fly from Boston Logan International to Chicago O'Hare International?

3 hours and 4 minutes is the average flight time from Boston Logan International to Chicago O'Hare International.

Which airlines fly direct from Boston Logan International to Chicago O'Hare International?

American Airlines, United and Qatar Airways fly direct from Boston Logan International to Chicago O'Hare International.

How many flights are there a week from Boston Logan International to Chicago O'Hare International?

As of September 2026, there are 643 flights per week flying from Boston Logan International to Chicago O'Hare International.

When is the cheapest time to fly from Boston Logan International to Chicago O'Hare International?

The cheapest month to fly from Boston Logan International to Chicago O'Hare International is usually December.

Which upcoming date is cheapest to fly from Boston Logan International Airport to Chicago O'Hare International Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Boston Logan International Airport to Chicago O'Hare International Airport on Saturday, 5 December 2026.

Can I get a direct flight from Boston Logan International Airport to Chicago O'Hare International Airport?

Yes – the average flight time is 3 hours and 4 minutes.

How can I find the best flight deal to Chicago O'Hare International?

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 O'Hare International 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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Boston Logan International Airport to Chicago O'Hare International with?

Currently, Frontier Airlines and jetBlue offer the cheapest flight tickets to Chicago O'Hare International.

Flying from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD): what you need to know

The average duration of a direct flight from Boston Logan International Airport to Chicago O'Hare International Airport is 3 hours.
The timezone in Chicago is UTC-6, which is one hour behind Boston.
Each week, there are 157 Boston Logan International Airport to Chicago O'Hare International Airport flights. If you'd like to be on board early, jump on the 05:00 American Airlines flight. If you're eager to make the most of your day before flying, the last flight is at 21:31 with United Airlines.
Your BOS to ORD flight won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.
Travelling during a peak month like July? School holidays and other high seasons can result in longer lines and delays at security. Play it safe and arrive up to four hours ahead of an international flight and two hours before a domestic departure.
A number of airlines operate direct flights from Boston Logan International Airport to Chicago O'Hare International Airport, so jetting off to Chicago (and then discovering more of the United States!) is easy. The most popular carriers that fly nonstop include:
United is the airline most travellers choose to fly with on this route.
With 73.89% of its services landing on schedule, United is the most punctual carrier offering BOS to ORD flights.
Think about adding a stopover when booking your ticket from Boston Logan International Airport to Chicago O'Hare International Airport. Just uncheck 'Direct flights only' to break up your journey, or enjoy a detour to a new and interesting place. Here are some options between BOS and ORD:
- Detroit Wayne County Airport
- Baltimore Washington International Airport
- Pittsburgh International Airport

How to find the cheapest flights from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD)

$119 is currently the best price for a one-way Boston Logan International Airport to Chicago O'Hare International Airport flight. A return flight starts at $237. These fares can change based on demand and availability.
To get cheap tickets from BOS to ORD, book your journey one month before your departure date.
June is the cheapest month for flights from Boston Logan International Airport to Chicago O'Hare International Airport. If you want to fly during a different time of year, the 'Whole month' tool will show you the lowest prices for each month.
You won't have to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll update you the moment there's a new deal on cheap flights from BOS to ORD.
Find the ideal flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Boston Logan International Airport to Chicago O'Hare International Airport, use the 'Sort by' function. You can also filter by airline, arrival and departure times, and journey duration.

Handy information about Boston Logan International Airport (BOS)

You'll find BOS at One Harborside Drive.
When it comes to Boston Logan International Airport's on-time performance, data shows 75% of flights stick to their scheduled arrival time.
Boston Logan International Airport is about 8 kilometres from central Boston. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 20 minutes or so to get there, depending on the traffic.
Planning to take public transport? Expect a trip time of around 25 minutes.
Looking for a handy hotel close to BOS? If you're boarding an early flight from Boston Logan International Airport to Chicago O'Hare International Airport, these stays will have you sleeping moments from your check-in counter:

Arriving at Chicago O'Hare International Airport (ORD)

The last thing you want is a long trip to your hotel if you're getting in late on a Boston Logan International Airport to Chicago O'Hare International Airport flight. Reserve one of these accommodation options near ORD instead:
Grab a Chicago O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are well-known companies you can book with here.
To get the best deal, reserve your vehicle from Chicago O'Hare International Airport about four weeks before travelling.

When to fly to Chicago O'Hare International Airport (ORD)

July is the busiest month for flights from Boston Logan International Airport to Chicago O'Hare International Airport. To escape the crowds, head to Chicago in March.
The warmest month in Chicago is July, with the temperature ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your flights from Boston Logan International Airport to Chicago O'Hare International Airport in this month if this is the kind of weather you like.
If you'd rather travel in cooler conditions, look for a cheap ticket from BOS to ORD in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of the United States

You've done Chicago, now it's time to explore more of the United States. Travel about 451 kilometres south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you on the go.
If you're looking to explore another great destination in the United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among the biggest draws.