Are there direct flights from Chicago to Boston?

Yes, direct flights are available from Chicago to Boston. Historically, approximately 51.8% of flights on this route have been direct. For flights that include stopovers, the median number of stopovers observed was 2.

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

The typical direct flight from Chicago to Boston has a median duration of 2 hours and 27 minutes. For flights with one stop, the median travel time is considerably longer, averaging 11 hours and 41 minutes. The air distance between Chicago and Boston is approximately 1391 kilometers.

How often do Chicago to Boston flight prices drop?

Historically, flight prices for the Chicago to Boston route tend to drop frequently. This indicates that travelers may often find opportunities for price reductions. Monitoring prices can be beneficial for securing a more favorable fare.

Flights From Chicago

To Boston

Cheap Flights from Chicago to Boston

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

Deals from

Chicago

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

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 Chicago to Boston

Explore current cheapest deals departing from Chicago to Boston

2026-12-11 – 2026-12-14
CHI - Boston
83% AI deal score
$367
$181
Round trip
2026-08-12 – 2026-08-18
CHI - Boston
68% AI deal score
$226
$191
Round trip
2026-10-15 – 2026-10-19
CHI - Boston
76% AI deal score
$292
$193
Round trip
2026-10-01 – 2026-10-03
CHI - Boston
72% AI deal score
$291
$195
Round trip
2026-10-14 – 2026-10-21
CHI - Boston
45% AI deal score
$176
$196
Round trip
2026-12-12 – 2026-12-14
CHI - Boston
81% AI deal score
$377
$196
Round trip
2026-08-08 – 2026-08-11
CHI - Boston
75% AI deal score
$278
$198
Round trip
2026-10-16 – 2026-10-23
CHI - Boston
71% AI deal score
$284
$199
Round trip
2026-10-10 – 2026-10-16
CHI - Boston
70% AI deal score
$281
$202
Round trip
2026-08-18 – 2026-08-28
CHI - Boston
49% AI deal score
$202
$203
Round trip

Chicago to Boston: Overview

Insights for flights from Chicago to Boston

Flights from Chicago to Boston cover a distance of 1,391 kilometers, classifying this as a short-haul route. For travelers seeking cheap flights from Chicago to Boston, fares typically range from $215–$582, with a median price of $319. Right now, current fares are significantly above the typical level, and only 1% of recent fares were classified as a good price. New deals appear almost daily for this route.

When is the cheapest time to fly from Chicago to Boston? The data shows that December is the most affordable month, with a median fare of just $103. Following December, August offers a median fare of $217, and September is also a good option with a median of $228.

Regarding direct flights from Chicago to Boston, 51.8% of recent itineraries are non-stop, meaning a meaningful share are non-stop, while the rest connect at least once. For itineraries that include connections, the typical number of stopovers is 2.

How long is the flight from Chicago to Boston? A typical journey, including connecting itineraries, takes approximately 2h 27m. Non-stop flights also have a median duration of 2h 27m, while connecting flights typically take much longer, with a median of 14h 56m.

How much is a round trip from Chicago to Boston

Regular price: $267 - $394

Prices are currently below the regular range.

Regular prices for flights from Chicago to Boston typically range from $267 to $394. The current lowest deal is $181 with JetBlue Airways for travel from Dec 11-Dec 14.

now $181

Low $267

High $394

The cheapest time to fly from Chicago to Boston

The cheapest month to fly from Chicago to Boston is December, with a median price of $103. The most expensive month is July, with a median price of $493. Prices are generally lower from January to December.

December

Cheapest

Flights from $103

July

Most Expensive

Flights from $493

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Boston

JetBlue Airways

Last-minute flights going from Chicago to Boston

Tue, Jul 28

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

Deutsche Luft Hansa

$383

$317

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - Boston

Chicago (MDW) - Boston (BOS)

Deutsche Luft Hansa

$461

$275

One-way

Sat, Aug 8

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$271

$198

One-way

Mon, Aug 10

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$256

$205

One-way

Wed, Aug 12

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$225

$191

One-way

Thu, Aug 13

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$248

$207

One-way

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

3 nights

Dec 11 - Dec 14

$375 → $181

52%

4 nights

Aug 1 - Aug 5

$461 → $275

40%

2 nights

Dec 12 - Dec 14

$375 → $196

48%

11 nights

Dec 14 - Dec 25

$344 → $236

31%

Popular Airports to fly from Chicago to Boston

Chicago - Boston route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Boston are below the typical level at $181.

📅 Best time to fly

Fly in December for the best prices

Historically, December is the cheapest month to fly, with a median price of $103.

⏱️ Flight duration

Direct flights average 2h 27m

Direct flights from Chicago to Boston typically take 2 hours and 27 minutes.

✈️ Airlines & availability

Direct flights are available

Approximately 51.8% of recent flights on this route are direct.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways is a provider of direct flights on the Chicago to Boston route.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Boston are frequently available.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Consider O'Hare International for flights from Chicago to Boston, often offering competitive prices.

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

💸 Flights from ~$139

Chicago Midway International (MDW)

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

📍 ~14 km from Chicago city center (reachable by car or train)

💸 Flights from ~$141

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative for flights from Chicago to Boston.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$308

Boston main airports to arrive at

Logan International (BOS)

Cheapest

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

📍 ~4 km from Boston city center (reachable by car)

💸 Flights from ~$139

Airports nearby Boston used as alternative

Rhode Island T. F. Green Int'l Airport (PVD)

Rhode Island T. F. Green Int'l Airport is a major regional hub that can help you avoid Boston Logan's congestion.

📍 ~70 km from Boston (reachable by car)

💸 Flights from ~$213

Business & First Class Flight Deals to Boston

69% AI deal score

$629

$517

Save $112

Frequently Asked Questions About Flights to Boston

Historically, the optimal booking window for flights from Chicago to Boston is typically 14-27 days before departure. During this period, the average price observed was $287. Booking within 7-13 days of departure saw average prices around $334, while booking 60+ days out resulted in an average price of $336. Flights booked 0-6 days before departure were the most expensive, averaging $379.

Based on historical data for flights from Chicago to Boston, a good price is considered to be $215 or less. The median price observed across the trailing quarter was $319. Prices can vary, with 75% of fares being $582 or less.

Historically, December has shown the cheapest flights from Chicago to Boston, with a median price of $103. August and September also offer relatively lower prices, with median fares of $217 and $228 respectively. The annual median price for this route is $319, indicating that these months typically provide better value for travelers.

Chicago to Boston: Overview

Insights for flights from Chicago to Boston

How much is a round trip from Chicago to Boston

Regular price: $267 - $394

Prices are currently below the regular range.

Regular prices for flights from Chicago to Boston typically range from $267 to $394. The current lowest deal is $181 with JetBlue Airways for travel from Dec 11-Dec 14.

now $181

Low $267

High $394

The cheapest time to fly from Chicago to Boston

December

Cheapest

Flights from $103

July

Most Expensive

Flights from $493

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec