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

Across the trailing quarter, approximately 44.8% of flights from Boston to Chicago are non-stop. For travelers who opt for connecting flights, the median number of stopovers observed is 2. This indicates that while direct options are available, a significant portion of the routes involve at least one connection. Travelers should consider their preferences for direct versus connecting flights when planning their journey.

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

A direct flight from Boston to Chicago typically takes 2 hours and 58 minutes. This is based on a median direct flight time of 178 minutes. For flights with one stop, the median travel time increases significantly to 11 hours and 1 minute, or 661 minutes. The route covers a distance of 1382 kilometers, making direct flights a considerably faster option.

How often do Boston to Chicago flight prices drop?

Historically, flight prices for the Boston to Chicago route tend to drop frequently. This route is categorized as one with frequent price fluctuations. Travelers monitoring this route may observe price changes regularly, indicating opportunities to find more favorable fares. This frequent movement in pricing can be beneficial for those looking to secure a good deal.

Flights From Boston

To Chicago

Cheap Flights from Boston to Chicago

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Deals from

Boston

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

Prices updated 1 day ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Boston to Chicago

Explore current cheapest deals departing from Boston to Chicago

2026-10-17 – 2026-10-31
BOS - Chicago
45% AI deal score
$118
$180
Round trip
2026-10-27 – 2026-10-31
BOS - Chicago
46% AI deal score
$144
$180
Round trip
2026-10-07 – 2026-10-14
BOS - Chicago
46% AI deal score
$138
$180
Round trip
2026-10-20 – 2026-10-27
BOS - Chicago
46% AI deal score
$137
$180
Round trip
2026-10-15 – 2026-10-19
BOS - Chicago
46% AI deal score
$145
$180
Round trip
2026-10-15 – 2026-10-16
BOS - Chicago
46% AI deal score
$145
$180
Round trip
2026-10-13 – 2026-10-14
BOS - Chicago
46% AI deal score
$145
$180
Round trip
2026-10-10 – 2026-10-13
BOS - Chicago
46% AI deal score
$145
$180
Round trip
2026-10-10 – 2026-10-17
BOS - Chicago
46% AI deal score
$138
$180
Round trip
2026-10-16 – 2026-10-19
BOS - Chicago
46% AI deal score
$145
$180
Round trip

Boston to Chicago: Overview

Insights for flights from Boston to Chicago

For travelers seeking cheap flights from Boston to Chicago, fares typically range from $201 to $612, with a median of $351. Right now, current fares are above the typical level for this route. Only about 3% of recent fares were classified as a good price, indicating that finding particularly low prices can be challenging.

When is the cheapest time to fly from Boston to Chicago? The data indicates that November is typically the most affordable month, with a median fare of $103. Following closely, January offers a median fare of $111, and February presents a median of $143. These months generally provide better value for this route.

A meaningful share of itineraries between Boston and Chicago are non-stop, with 44.8% of recent fares being direct flights from Boston to Chicago. For the remaining itineraries, most connecting flights typically involve 2 stopovers.

The typical journey time for flights from Boston to Chicago is 2h 58m. This duration represents the median flight time for all itineraries, including both direct and connecting options. For non-stop flights, the median time is also 2h 58m, while connecting itineraries have a significantly longer median duration of 14h 59m.

The distance between Boston and Chicago is approximately 1382 kilometers. This classifies the route as a short-haul journey, meaning it is a relatively brief flight.

How much is a round trip from Boston to Chicago

Regular price: $96 - $242

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

The regular price range for flights from Boston to Chicago is $96 to $242. The current lowest deal is $189 with Southwest Airlines for travel from Nov 11-Nov 18.

now $189

Low $96

High $242

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, Sep 17

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

Frontier Airlines

$437

$317

One-way

Thu, Sep 17

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$439

$356

One-way

Sat, Sep 19

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

Frontier Airlines

$413

$320

One-way

Sat, Sep 19

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

Frontier Airlines

$415

$320

One-way

Sat, Sep 19

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$439

$336

One-way

Sat, Sep 19

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$437

$338

One-way

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

1 night

Sep 15 - Sep 16

$439 → $298

32%

3 nights

Sep 15 - Sep 18

$433 → $298

31%

2 nights

Sep 17 - Sep 19

$419 → $285

32%

4 nights

Sep 14 - Sep 18

$430 → $297

31%

Popular Airports to fly from Boston to Chicago

Boston - Chicago route insights

💸 Price insights

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

Recent fares for Boston to Chicago are above the typical level, with a median price of $351.

📅 Best time to fly

Fly in November for the lowest median prices.

Historically, November, January, and February offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 2h 58m.

Direct flights from Boston to Chicago typically take 2 hours and 58 minutes.

✈️ Airlines & availability

Direct flights are available from JetBlue Airways.

JetBlue Airways offers direct flights on this route, with 44.8% of recent flights being direct.

🏆 Airline highlight

JetBlue Airways offers direct flights on this route.

JetBlue Airways has direct flights from Boston to Chicago, with deals available.

🎯 Booking tip

Deals are frequent for Boston to Chicago.

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

Boston main airports to depart from

Logan International (BOS)

Cheapest

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

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

💸 Flights from ~$178

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient arrival option for flights from Boston to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$178

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$276

Business & First Class Flight Deals to Chicago

78% AI deal score

$998

$535

Save $463

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 most favorable within a few weeks of the travel date, rather than months in advance.

Across the trailing quarter, a flight from Boston to Chicago is considered a good deal if you find it for $201 or less. This price point represents the lower quartile of observed fares. The median price for this route historically stands at $351, while prices in the upper quartile can reach $612 or more. Aiming for fares at or below $201 will help ensure you are getting a competitive price.

Historically, the cheapest months to fly from Boston to Chicago are November, January, and February. November typically sees a median price of $103, while January has a median of $111. February also offers competitive pricing, with a median of $143. These months generally offer more affordable options compared to the annual median price of $351 for this route.

Related routes

More routes from Boston

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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

The distance between Boston and Chicago is approximately 1382 kilometers. This classifies the route as a short-haul journey, meaning it is a relatively brief flight.

How much is a round trip from Boston to Chicago

Regular price: $96 - $242

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

The regular price range for flights from Boston to Chicago is $96 to $242. The current lowest deal is $189 with Southwest Airlines for travel from Nov 11-Nov 18.

now $189

Low $96

High $242

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