Route Price Intelligence

Cheap Flights From Boston to Chicago

Live pricing benchmarks, monthly patterns, and historical lows for this route.

⭐ Great DealFound 2d ago

$225

American is flying Providence to Chicago nonstop for $225, about 42% off the usual $389 fare. Chicago's lakefront, deep dish, and architecture boat tours are all an easy nonstop hop away, with dates open over the next several months. It is one of the cleaner nonstop discounts we have seen on this route lately.

✓ 14 date combinations found at this price

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Typical Price

$205

Great Deal

Under $186

Typical Range

$186 – $206

Lowest We've Seen

$94

Based on 271 price pointshigh confidence

Monthly Price Guide

Jan

$205

Feb

—

Mar

—

Apr

$201

May

$173

Jun

$186

Jul

$177

Aug

$186

Sep

$205

Oct

$205

Nov

$205

Dec

$205

Cheapest Average Expensive

Best Time to Fly from Boston to Chicago

The cheapest time to fly from Boston to Chicago is typically May, when fares average around $173. The most expensive month tends to be September at around $205. For the best deals, consider flying in May, July, June.

Typical Price by Travel Month

Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route

Cheapest month: September43,519 fares analyzedTypical low: $171

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