Cheap Flights from Chicago Midway to Boston Logan International in 2019

Flight information Chicago Midway to Boston Logan International

Non-stop airline


Flights per week


Average flight time, total distance 858 miles

2h 10min

Most popular airline last month

Southwest Airlines

Boston Logan International

1 airport

Explore Boston

Boston Hotels

When it comes to history and culture, Beantown is hard to beat. The trip from Chicago to Boston is just under 1,000 miles. In terms of in-flight time, you’re looking at an average of two and a half hours in the air.

If you begin your journey from Chicago Midway Airport (MDW), you can grab a nonstop flight to Boston Logan (BOS)with Southwest, which offers 36 weekly flights on the route.

Making your way to Chicago’s airports

Flying from Chicago Midway is often recommended for short flights, since the airport is so much smaller and very convenient. You can also often find cheaper fares from Midway than its larger Chicago airport counterpart, O’Hare. Midway is only 8 miles from downtown, and is also connected to the CTA Blue Lineby the Orange Line train. Once you get to the airport, you’ll have a 10 to 15 minute walk through a tunnel to main terminal building.

There is free WiFi available, but it is extremely limited. You can access about 30 pages for free, but for actual unlimited and unrestricted internet, you’ll need to pay a daily fee of $6.85.

Arriving in Boston

The revolutionary war takes central stage in Boston’s long story, and it seems as though every block was home to some momentous event or another. You can retrace the patriot’s footsteps on the Freedom Trail, a self-guided tour of the most important historical sites in the city. As a bonus, it winds through some amazing neighborhoods like Beacon Hill, where lamps still light the cobblestone streets.

It’s not all monuments and minutemen, though. Modern Boston is vibrant, exciting, and full of fun. Catch a Red Sox game in one of the city’s hundreds of Irish Bars, or in Fenway itself, if you can find a ticket. Visit one of the many incredible museums: the Institute of Contemporary Art, on the waterfront, is a special gem. Take a trip over the Charles River to Cambridge and stroll through Harvard Yard. Wherever you go in the Boston area, you’ll encounter the big, brave, friendly personality of this great city.

Find the very cheapest tickets from Chicago to Boston with Skyscanner’s airfare comparison tool. It’s free, it’s easy, and it only takes a few seconds to round up the best deal on your flights.

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