- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Cheapest price on Oct 08
€221
Average ticket price on Oct 08
€407
Fastest journey on Oct 08
2 h 52 m
Average journey duration on Oct 08
2 h 53 m
Flights on Oct 08
60
Distance
1368 km
The best way to find a cheap flight ticket from Boston, MA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Boston, MA to Chicago, IL will cost around €407 if you buy it on the day, but the cheapest tickets can be found for only €221.
On Thu, Oct 08, we found 60 flights from Boston, MA to Chicago, IL, including 20 direct services.
On Thu, Oct 08 the direct flights cover the 1368 km distance in an average of 2 h 53 m but if you time it right, some flights will get you there in just 2 h 52 m .
On Thu, Oct 08 the longest flights will take 2 h 55 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
UA1349
UA2631
UA1414
UA1734 · UA1775
UA1734 · UA1252
UA1732
UA1349
UA1475
UA503
UA1097Flights from Boston, MA to Chicago, IL depart on average 60 times per day, taking around 4h 38m. Cheap flight tickets for this journey start at €43 if you book in advance.
There are 16 flights per day. The earliest flight runs at 00:06, the last at 22:34. The fastest flight covers the 850 miles (1368 km) distance in 2h 48m. July is the cheapest month to fly.
Distance 850 miles (1368 km) |
Average flight duration 4h 38m |
Cheapest ticket price €43 |
Flights per day 60 |
Direct flights 16 |
Fastest flight 2h 48m |
First flight 12:06 AM |
Last flight 10:34 PM |
Cheapest Month Jul |
Cheapest Day Thu |
High Season Jul - Sep |
Low Season Jan - Mar |
Busiest Day Thu |
Least Busy Day Fri |
Best time to book 28 days |
The table below shows live departures for Boston, MA to Chicago, IL flights for today, Wednesday, October 7. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:27 AM Boston, MA | 14h44 | 12:11 AM Chicago, IL | 0 transfersDirect | |
![]() | 9:31 AM Boston, MA | 2h59 | 12:30 PM Chicago, IL | 0 transfersDirect | |
![]() | 10:05 AM Boston, MA | 3h00 | 1:05 PM Chicago, IL | 0 transfersDirect | |
![]() | 12:00 PM Boston, MA | 13h41 | 1:41 AM Chicago, IL | 0 transfersDirect | |
![]() | 8:34 PM Boston, MA | 3h17 | 11:51 PM Chicago, IL | 0 transfersDirect | |
![]() | 10:47 PM Boston, MA | 3h06 | 1:53 AM Chicago, IL | 0 transfersDirect | |
![]() | 11:35 PM Boston, MA | 3h01 | 2:36 AM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Find answers to the most common questions about traveling from Boston, MA to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Boston, MA to Chicago, IL flights use the Edward L. Logan International Airport to O'Hare International Airport airport pair. Use this guide to compare Boston, MA and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Edward L. Logan International Airport is 2 km from Boston city centre. Public transport options include:
Edward L. Logan International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are available in all terminals, including Legal Sea Foods (seafood) and Wahlburgers (American).
Free Wi-Fi available throughout the airport. ATMs are located throughout the airport, near gates and publicas.
Lost and found is available at the station.
Available at Edward L. Logan International Airport: Parking, Taxis, WC.
Available at Edward L. Logan International Airport: Car Rental.
Accessibility facilities are available at Edward L. Logan International Airport: Elevators, ramps.
Nearby hotels include Hotels within walking distance, including Hilton Boston Logan Airport..
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Here are some other resources that might have the information you need