How many flights from Boston to Chicago are non-stop?

In the trailing 90 days, approximately 44.8% of flights from Boston to Chicago were non-stop. For flights that included stopovers, the median number of stopovers was 2. This indicates that while direct flights are common, a significant portion of routes involve at least one connection. Travelers should consider this when planning their journey.

How long does it take to fly from Boston to Chicago?

The typical direct flight from Boston to Chicago has a median duration of 2 hours and 58 minutes. For flights with one stop, the median travel time increases significantly to 11 hours and 1 minute. The air distance between these two cities is approximately 1382 kilometers. Travelers should factor in these durations when choosing between direct and connecting flights.

How often do Boston to Chicago flight prices drop?

Historically, flight prices for the Boston to Chicago route have shown frequent drops. This indicates that travelers may often find opportunities to secure more favorable fares. Regular monitoring of prices is advisable for those seeking to find a good deal on this route. The frequent price fluctuations suggest a dynamic market for this popular travel corridor.

Flights From Boston

To Chicago

Cheap Flights from Boston to Chicago

Browse current best options from Boston. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Boston

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Boston to Chicago

Explore current cheapest deals departing from Boston to Chicago

2026-09-06 – 2026-09-14
BOS - Chicago
68% AI deal score
$211
$183
Round trip
2026-11-11 – 2026-11-14
BOS - Chicago
45% AI deal score
$136
$187
Round trip
2026-09-03 – 2026-09-10
BOS - Chicago
68% AI deal score
$223
$188
Round trip
2026-10-03 – 2026-10-07
BOS - Chicago
70% AI deal score
$251
$189
Round trip
2026-09-12 – 2026-09-15
BOS - Chicago
69% AI deal score
$234
$190
Round trip
2026-09-14 – 2026-09-24
BOS - Chicago
65% AI deal score
$199
$190
Round trip
2026-09-25 – 2026-09-28
BOS - Chicago
69% AI deal score
$236
$191
Round trip
2026-10-20 – 2026-10-22
BOS - Chicago
70% AI deal score
$253
$191
Round trip
2026-09-12 – 2026-09-19
BOS - Chicago
68% AI deal score
$222
$193
Round trip
2026-09-28 – 2026-09-30
BOS - Chicago
69% AI deal score
$235
$193
Round trip

Boston to Chicago: Overview

Insights for flights from Boston to Chicago

Flights from Boston to Chicago typically range from $201–$612, with a median fare of $351. Right now, fares are above the typical level, and only 3% of recent fares were classified as a good price. For travelers seeking cheap flights from Boston to Chicago, new deals appear almost daily, suggesting frequent opportunities to find better prices.

When considering the cheapest time to fly from Boston to Chicago, November stands out with a median fare of just $103. Following closely, January offers median fares around $111, and February presents a median of $143. These months generally offer the most budget-friendly options for this route.

For this route, a meaningful share of itineraries are non-stop, while the rest connect once. Specifically, 44.8% of recent fares from Boston to Chicago were for direct flights. For itineraries that do include connections, the typical number of stopovers is 2.

The typical journey time for flights from Boston to Chicago, including connections, is approximately 2h 58m. This duration reflects the overall travel time, encompassing both direct flights and those with layovers, providing a comprehensive view of the expected trip length.

The distance between Boston and Chicago is 1382 kilometers, classifying this as a short-haul route. This distance typically translates to a relatively quick flight, making it a convenient option for travelers.

How much is a round trip from Boston to Chicago

Regular price: $168 - $301

Prices for flights from Boston to Chicago are currently within the regular range.

The regular price range for flights from Boston to Chicago is between $168 and $301. The current lowest deal is $183 with JetBlue Airways for travel from Sep 6-Sep 14.

now $183

Low $168

High $301

The cheapest time to fly from Boston to Chicago

The cheapest month to fly from Boston to Chicago is January, with a median price of $148. The most expensive month is December, with a median price of $1118. Prices are generally lower from January to November.

January

Cheapest

Flights from $148

December

Most Expensive

Flights from $1,118

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Boston to Chicago

JetBlue Airways

Last-minute flights going from Boston to Chicago

Thu, Jul 30

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$392

$280

One-way

Sun, Aug 2

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Deutsche Luft Hansa

$321

$286

One-way

Sun, Aug 2

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Southwest Airlines

$420

$322

One-way

Mon, Aug 10

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$303

$237

One-way

Tue, Aug 11

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$227

$191

One-way

Tue, Aug 11

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$254

$199

One-way

Biggest price drops on these dates for flights from Boston to Chicago

4 nights

Dec 11 - Dec 15

$345 → $191

45%

1 night

Jul 30 - Jul 31

$392 → $280

29%

4 nights

Dec 10 - Dec 14

$338 → $237

30%

1 night

Aug 2 - Aug 3

$420 → $322

23%

Popular Airports to fly from Boston to Chicago

Boston - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Boston to Chicago are above the typical level at $351.

📅 Best time to fly

Fly in January for the best prices

Historically, January is the cheapest month to fly from Boston to Chicago, with a median price of $148.

⏱️ Flight duration

Direct flights take 2h 58m

The typical direct flight from Boston to Chicago takes 2h 58m, while connecting flights average 14h 59m.

✈️ Airlines & availability

44.8% of recent flights are direct

Historically, 44.8% of flights from Boston to Chicago are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways operates direct flights on the Boston to Chicago route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Boston to Chicago are frequent, appearing often over a 30-day window.

Boston main airports to depart from

Logan International (BOS)

Cheapest

Logan International is a convenient option for flights from Boston to Chicago.

📍 ~4 km from Boston (reachable by car or train)

💸 Flights from ~$141

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Boston, offering many options.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$135

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International Airport (MKE) is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by rail or car)

💸 Flights from ~$192

Business & First Class Flight Deals to Chicago

79% AI deal score

$1,097

$552

Save $545

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Boston to Chicago is typically 7-13 days before departure. During this period, the average price observed was $293. Booking within 0-6 days of departure saw an average price of $384, while booking 60+ days out resulted in a significantly higher average price of $642. Prices tend to be more favorable closer to the departure date, rather than booking far in advance.

Across the trailing quarter, a good price for a flight from Boston to Chicago was considered to be $201 or less. The median price for this route was $351, indicating that half of all observed prices were below this amount. Prices above $612 were in the most expensive quartile. Travelers aiming for a good deal should target prices at or below the $201 threshold.

Historically, the cheapest months to fly from Boston to Chicago have been November, January, and February. November showed a median price of $103, while January had a median of $111. February also offered a relatively low median price of $143. These months typically present more affordable options compared to the annual median price of $351 for this route.

Related routes

More routes from Boston

Flights from Boston to Cancún Flights from Boston to Cape Town Flights from Boston to Charleston Flights from Boston to Charlotte Flights from Boston to Cincinnati Flights from Boston to Cleveland Flights from Boston to Colorado Springs Flights from Boston to Copenhagen Flights from Boston to Dallas Flights from Boston to Dar es Salaam Flights from Boston to Denver Flights from Boston to New Delhi

Flights to Chicago from other cities

Flights from Cairo to Chicago Flights from Cancún to Chicago Flights from Cape Town to Chicago Flights from Casablanca to Chicago Flights from Charleston to Chicago Flights from Charlotte to Chicago Flights from Cincinnati to Chicago Flights from Cleveland to Chicago Flights from Colombo to Chicago Flights from Colorado Springs to Chicago Flights from Columbus to Chicago Flights from New Delhi to Chicago

Boston to Chicago: Overview

Insights for flights from Boston to Chicago

How much is a round trip from Boston to Chicago

Regular price: $168 - $301

Prices for flights from Boston to Chicago are currently within the regular range.

The regular price range for flights from Boston to Chicago is between $168 and $301. The current lowest deal is $183 with JetBlue Airways for travel from Sep 6-Sep 14.

now $183

Low $168

High $301

The cheapest time to fly from Boston to Chicago

January

Cheapest

Flights from $148

December

Most Expensive

Flights from $1,118

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec