$45 Cheap Flights from Boston to Chicago

Be sure to check out our Covid-19 Travel Advisor to see if there are any current quarantine requirements or travel advice reports in place in ORD when jet-setting from BOS.

Your next unforgettable adventure is on the other side of just one flight. You can jet direct from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) with multiple airlines, including United Airlines and American Airlines.

For more info about changing your flight to O’Hare Intl. Airport (ORD), please visit our Customer Service Portal.

If you were hoping to get some decent shut-eye during your Boston to Chicago flight, you may have to think again. The normal flight time between Logan Intl. Airport (BOS) and O’Hare Intl. Airport (ORD) is a quick 2 hours and 56 minutes — just enough to get comfortable and rest your eyes for a little while.

With a mere 860 mi separating BOS and ORD, there’ll be little time between the seat belt sign turning off and the captain readying the wheels for touchdown.

With a range of airlines operating direct flights from BOS to O’Hare Intl. Airport (ORD), you’re spoiled for choice. Here are some of the most well-known air carriers:

• United Airlines - (UA) with 208 flights every month
• American Airlines - (AA) with 195 flights every month
• Delta - (DL) with 147 flights every month
• JetBlue - (B6) with 56 flights every month

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with United Airlines, American Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.