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

In the trailing 90 days, approximately 28.1% of flights from Boston to Chicago were non-stop. For flights that include stopovers, travelers typically experience a median of 2 connections. This indicates that while direct options are available, a significant portion of routes involve at least one stop.

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

A direct flight from Boston to Chicago typically takes about 2 hours and 59 minutes, covering a distance of 1382 kilometers. Flights with one stop, however, have a significantly longer median duration, averaging around 10 hours and 39 minutes. Travelers should consider these differences when planning their journey.

How often do Boston to Chicago flight prices drop?

Historically, flight prices for the Boston to Chicago route tend to drop frequently. This suggests that travelers may have regular opportunities to find more affordable fares. Monitoring prices over time can be beneficial for securing a good deal on this route.

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 7 days ago

483 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Boston to Chicago

Explore current cheapest deals departing from Boston to Chicago

2026-12-10 – 2026-12-17
BOS - Chicago
71% AI deal score
$263
$186
Round trip
2026-11-17 – 2026-11-21
BOS - Chicago
66% AI deal score
$249
$197
Round trip
2026-11-18 – 2026-11-21
BOS - Chicago
66% AI deal score
$248
$197
Round trip
2026-12-03 – 2026-12-06
BOS - Chicago
68% AI deal score
$279
$204
Round trip
2026-11-14 – 2026-11-21
BOS - Chicago
46% AI deal score
$233
$217
Round trip
2026-11-19 – 2026-11-21
BOS - Chicago
46% AI deal score
$246
$231
Round trip
2026-11-19 – 2026-11-25
BOS - Chicago
44% AI deal score
$232
$231
Round trip
2026-12-10 – 2026-12-12
BOS - Chicago
50% AI deal score
$283
$231
Round trip
2026-12-02 – 2026-12-07
BOS - Chicago
66% AI deal score
$273
$232
Round trip
2026-12-11 – 2026-12-12
BOS - Chicago
48% AI deal score
$280
$235
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 $362–$846, with a median of $563. Right now, fares are above the typical level. New deals appear almost daily, offering frequent opportunities to find flights.

When is the cheapest time to fly from Boston to Chicago? The data indicates that January is the most affordable month, with a median fare of $190. Following closely, March offers a median fare of $260, and May presents a median of $331, making these months generally more economical for this route.

Regarding direct flights from Boston to Chicago, most itineraries connect at least once, with only 28.1% of recent fares being non-stop. For connecting itineraries, the typical number of connections is 2.

How long is the flight from Boston to Chicago? A typical journey, including connections, takes approximately 20h 44m. For non-stop flights, the median duration is 2h 59m, while connecting flights have a median duration of 20h 44m.

The route from Boston to Chicago covers a distance of 1382 kilometers, classifying it as a short-haul flight.

How much is a round trip from Boston to Chicago

Regular price: $189 - $293

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 $189 and $293. The current lowest deal is $197 with Frontier Airlines for travel from Nov 18-Nov 24.

now $197

Low $189

High $293

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 $190. The most expensive month is December, with a median price of $899. Prices are generally lower from January to October.

January

Cheapest

Flights from $190

December

Most Expensive

Flights from $899

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Boston to Chicago

JetBlue Airways

Last-minute flights going from Boston to Chicago

Mon, Oct 26

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$468

$383

One-way

Mon, Oct 26

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$278

$434

One-way

Tue, Oct 27

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$459

$377

One-way

Tue, Oct 27

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (MDW)

Frontier Airlines

$470

$377

One-way

Tue, Oct 27

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$272

$434

One-way

Tue, Oct 27

⌛ Last-Minute

BOS - Chicago

Boston (BOS) - Chicago (ORD)

JetBlue Airways

$279

$434

One-way

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

3 nights

Oct 27 - Oct 30

$462 → $350

24%

2 nights

Oct 28 - Oct 30

$468 → $356

24%

4 nights

Oct 27 - Oct 31

$459 → $377

18%

2 nights

Oct 29 - Oct 31

$451 → $383

15%

Popular Airports to fly from Boston to Chicago

Boston - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Boston to Chicago are above the typical level of $563.

📅 Best time to fly

Fly in January for prices as low as $190

Historically, January, March, and May offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 2h 59m

Connecting flights typically take 20h 44m, with 28.1% of flights being direct.

✈️ Airlines & availability

Connecting flights are dominant

Most flights from Boston to Chicago include at least one stopover.

🏆 Airline highlight

Frontier Airlines offers a deal for $197

A recent deal from Frontier Airlines was found for travel from November 18-24.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Boston to Chicago appear frequently, so check often.

Boston main airports to depart from

Logan International (BOS)

Cheapest

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

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

💸 Flights from ~$221

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights from Boston to Chicago.

📍 ~14 km from Chicago (reachable by car)

💸 Flights from ~$201

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$327

Business & First Class Flight Deals to Chicago

75% AI deal score

$719

$473

Save $246

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Boston to Chicago is typically 28-59 days before departure. During this period, the average price observed was $616. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging around $925. Planning ahead can lead to more favorable pricing.

Across the trailing quarter, a flight from Boston to Chicago is considered a good deal if it is priced at or below $362. The median price for this route historically stands at $563. Prices can go higher, with 75% of observed prices being $846 or less, so finding a fare at or below the good price threshold represents significant savings.

Historically, January, March, and May have offered some of the lowest median prices for flights from Boston to Chicago. January typically sees a median price of $190, while March averages around $260. The annual median price for this route is $563, indicating that these months often present more economical travel opportunities.

Related routes

More routes from Boston

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Flights to Chicago from other cities

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Boston to Chicago: Overview

Insights for flights from Boston to Chicago

The route from Boston to Chicago covers a distance of 1382 kilometers, classifying it as a short-haul flight.

How much is a round trip from Boston to Chicago

Regular price: $189 - $293

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 $189 and $293. The current lowest deal is $197 with Frontier Airlines for travel from Nov 18-Nov 24.

now $197

Low $189

High $293

The cheapest time to fly from Boston to Chicago

January

Cheapest

Flights from $190

December

Most Expensive

Flights from $899

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec