Are there direct flights from Raleigh to Chicago?

Direct flights from Raleigh to Chicago are available, making up 17% of all flights on this route. For flights that include stopovers, travelers typically encounter 2 stopovers. This data reflects trends observed across the trailing 90 days.

How many hours is the flight from Raleigh to Chicago?

The typical direct flight from Raleigh to Chicago has a duration of 2 hours and 30 minutes. For flights with one stop, the median travel time increases significantly to 6 hours and 59 minutes. The distance covered on this route is approximately 1016 kilometers.

How often do cheap flights from Raleigh to Chicago come up?

Cheap flights from Raleigh to Chicago are categorized as frequent. This suggests that favorable deals for this route appear regularly. Travelers can typically find good opportunities for this route across the trailing quarter.

Flights From Raleigh

To Chicago

Cheap Flights from Raleigh to Chicago

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

Deals from

Raleigh

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

Prices updated 1 day ago

457 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 7, 2026.)

Today’s best flight deals from Raleigh to Chicago

Explore current cheapest deals departing from Raleigh to Chicago

2026-09-21 – 2026-09-23
RDU - Chicago
45% AI deal score
$229
$207
Round trip
2026-09-10 – 2026-09-16
RDU - Chicago
71% AI deal score
$282
$207
Round trip
2026-10-05 – 2026-10-07
RDU - Chicago
46% AI deal score
$232
$207
Round trip
2026-09-09 – 2026-09-10
RDU - Chicago
49% AI deal score
$270
$210
Round trip
2026-09-17 – 2026-09-24
RDU - Chicago
42% AI deal score
$215
$213
Round trip
2026-10-17 – 2026-10-21
RDU - Chicago
45% AI deal score
$231
$213
Round trip
2026-09-09 – 2026-10-04
RDU - Chicago
42% AI deal score
$196
$213
Round trip
2026-09-10 – 2026-09-12
RDU - Chicago
73% AI deal score
$315
$214
Round trip
2026-10-15 – 2026-10-21
RDU - Chicago
43% AI deal score
$220
$215
Round trip
2026-09-10 – 2026-10-04
RDU - Chicago
44% AI deal score
$219
$215
Round trip

Raleigh to Chicago: Overview

Insights for flights from Raleigh to Chicago

Only 1% of recent fares from Raleigh to Chicago were classified as a good price. Right now, fares are above the typical level, with prices typically ranging from $176–$532 and a median of $288. New deals appear almost daily for this route, so setting up a price alert can help you find cheap flights from Raleigh to Chicago.

When is the cheapest time to fly from Raleigh to Chicago? The data indicates that April is typically the most affordable month, with a median fare of $139. Following closely, February offers a median fare of $159, and August presents a median of $164.

A typical journey from Raleigh to Chicago takes about 2h 30m. However, since most itineraries connect at least once, a typical connecting journey can extend to 10h 29m. Only 17% of recent fares from Raleigh to Chicago were for direct flights, meaning most itineraries include at least one stopover, with a median of 2 connections when not flying direct.

The route from Raleigh to Chicago covers a distance of 1016 km. This classifies it as a short-haul journey, making it a relatively quick trip.

How much is a round trip from Raleigh to Chicago

Regular price: $184 - $288

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

Regular prices for flights from Raleigh to Chicago are between $184 and $288. The current lowest deal is $207 with Frontier Airlines for travel from Sep 21-Sep 23.

now $207

Low $184

High $288

The cheapest time to fly from Raleigh to Chicago

The cheapest month to fly from RDU to CHI is August, with a median price of $179. The most expensive month is January, with a median price of $772. Prices are generally lower from April to November.

August

Cheapest

Flights from $179

January

Most Expensive

Flights from $772

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Raleigh to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Raleigh to Chicago

Wed, Sep 2

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$453

$319

One-way

Wed, Sep 2

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$444

$325

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$397

$311

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$411

$319

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$409

$322

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$447

$337

One-way

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

3 nights

Oct 7 - Oct 10

$345 → $323

2 nights

Oct 31 - Nov 2

$339 → $323

4 nights

Oct 9 - Oct 13

$342 → $333

6 nights

Dec 30 - Jan 5

$316 → $323

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Raleigh to Chicago typically range from $176 to $532.

📅 Best time to fly

April, February, and August offer the lowest median prices

Historically, April, February, and August have offered median prices below $165.

⏱️ Flight duration

Direct flights average 2h 30m

Connecting flights typically take 10h 29m, with 2 stopovers on average.

✈️ Airlines & availability

Connecting flights are dominant on this route

Only 17% of recent flights from Raleigh to Chicago have been direct.

🏆 Airline highlight

Frontier Airlines offers a deal for $207

A recent deal from Frontier Airlines to Chicago was found for $207.

🎯 Booking tip

Deals appear frequently on this route

Historically, deals from Raleigh to Chicago have appeared frequently over the last 30 days.

Raleigh main airports to depart from

Raleigh–Durham International (RDU)

Cheapest

Raleigh–Durham International Airport is a convenient option for flights from Raleigh to Chicago.

📍 ~17 km from city center (reachable by car)

💸 Flights from ~$203

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers a budget-friendly option for flights from Raleigh to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$187

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Milwaukee (MKE) is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by train or car), requires travel across state lines into Wisconsin.

💸 Flights from ~$221

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Raleigh to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From RDU

Elite

Sep 06

Chicago, United States

74% AI deal score

$1,384

$884

Save $500

From RDU

Elite

Oct 07

Chicago, United States

67% AI deal score

$2,433

$1,868

Save $565

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Oct 07

Chicago, United States

67% AI deal score

$2,753

$1,991

Save $762

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Oct 13

Chicago, United States

66% AI deal score

$2,427

$2,032

Save $395

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Sep 11

Chicago, United States

66% AI deal score

$2,554

$2,156

Save $398

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Oct 25

Chicago, United States

65% AI deal score

$2,505

$2,029

Save $476

Air Canada, +1

Business Class

From RDU

Elite

Oct 14

Chicago, United States

65% AI deal score

$2,424

$2,029

Save $395

Air Canada, +1

Business Class

From RDU

Elite

Oct 27

Chicago, United States

65% AI deal score

$2,681

$2,160

Save $521

Air Canada, +1

Business Class

From RDU

Chicago, United States

50% AI deal score

$2,690

$2,306

Save $384

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Raleigh to Chicago is typically 28-59 days before departure. During this period, the average price for a flight is around $226. Booking within 0-6 days of departure sees prices rise significantly, with an average of $485. Even booking 60+ days out can result in higher average prices, around $307.

Across the trailing quarter, a good price for a flight from Raleigh to Chicago is considered to be $176 or less. The median price for this route over the same period was $288. Prices can go up to $532 or more, representing the higher end of fares in the trailing 90 days.

Historically, April is typically the cheapest month to fly from Raleigh to Chicago, with a median price of $139. February and August also offer competitive prices, with median fares of $159 and $164 respectively. The annual median price for this route is $288, indicating that these months offer significant savings.

Related routes

More routes from Raleigh

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Flights to Chicago from other cities

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Raleigh to Chicago: Overview

Insights for flights from Raleigh to Chicago

The route from Raleigh to Chicago covers a distance of 1016 km. This classifies it as a short-haul journey, making it a relatively quick trip.

How much is a round trip from Raleigh to Chicago

Regular price: $184 - $288

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

Regular prices for flights from Raleigh to Chicago are between $184 and $288. The current lowest deal is $207 with Frontier Airlines for travel from Sep 21-Sep 23.

now $207

Low $184

High $288

The cheapest time to fly from Raleigh to Chicago

The cheapest month to fly from RDU to CHI is August, with a median price of $179. The most expensive month is January, with a median price of $772. Prices are generally lower from April to November.

August

Cheapest

Flights from $179

January

Most Expensive

Flights from $772

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Raleigh to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Raleigh to Chicago

Wed, Sep 2

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$453

$319

One-way

Wed, Sep 2

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$444

$325

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$397

$311

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$411

$319

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$409

$322

One-way

Thu, Sep 3

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$447

$337

One-way

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

3 nights

Oct 7 - Oct 10

$345 → $323

2 nights

Oct 31 - Nov 2

$339 → $323

4 nights

Oct 9 - Oct 13

$342 → $333

6 nights

Dec 30 - Jan 5

$316 → $323

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Raleigh to Chicago typically range from $176 to $532.

📅 Best time to fly

April, February, and August offer the lowest median prices

Historically, April, February, and August have offered median prices below $165.

⏱️ Flight duration

Direct flights average 2h 30m

Connecting flights typically take 10h 29m, with 2 stopovers on average.

✈️ Airlines & availability

Connecting flights are dominant on this route

Only 17% of recent flights from Raleigh to Chicago have been direct.

🏆 Airline highlight

Frontier Airlines offers a deal for $207

A recent deal from Frontier Airlines to Chicago was found for $207.

🎯 Booking tip

Deals appear frequently on this route

Historically, deals from Raleigh to Chicago have appeared frequently over the last 30 days.

Raleigh main airports to depart from

Raleigh–Durham International (RDU)

Cheapest

Raleigh–Durham International Airport is a convenient option for flights from Raleigh to Chicago.

📍 ~17 km from city center (reachable by car)

💸 Flights from ~$203

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers a budget-friendly option for flights from Raleigh to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$187

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Milwaukee (MKE) is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by train or car), requires travel across state lines into Wisconsin.

💸 Flights from ~$221

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Raleigh to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From RDU

Chicago, United States

65% AI deal score

$974

$745

Save $229

From RDU

Elite

Oct 31

Chicago, United States

50% AI deal score

$2,535

$2,118

Save $417

Air Canada, +1

Business Class

From RDU

Elite

Nov 03

Chicago, United States

50% AI deal score

$2,591

$2,160

Save $431

Air Canada, +1

Business Class

From RDU

Elite

Oct 07

Chicago, United States

50% AI deal score

$2,690

$2,306

Save $384

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Raleigh to Chicago

Today’s best flight deals from Raleigh to Chicago

Raleigh to Chicago: Overview

Insights for flights from Raleigh to Chicago

How much is a round trip from Raleigh to Chicago

The cheapest time to fly from Raleigh to Chicago

Direct flights from Raleigh to Chicago

Last-minute flights going from Raleigh to Chicago

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

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

Recent fares are near the typical level

April, February, and August offer the lowest median prices

Direct flights average 2h 30m

Connecting flights are dominant on this route

Frontier Airlines offers a deal for $207

Deals appear frequently on this route

Raleigh main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 06

Oct 07

Oct 07

Oct 13

Sep 11

Oct 25

Oct 14

Oct 27

Dec 21

Oct 31

Nov 03

Oct 07

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Raleigh to Chicago?

What's a cheap fare from Raleigh to Chicago?

What's the cheapest month to fly from Raleigh to Chicago?

Are there direct flights from Raleigh to Chicago?

How many hours is the flight from Raleigh to Chicago?

How often do cheap flights from Raleigh to Chicago come up?

Related routes

More routes from Raleigh

Flights to Chicago from other cities

Raleigh to Chicago: Overview

Insights for flights from Raleigh to Chicago

How much is a round trip from Raleigh to Chicago

The cheapest time to fly from Raleigh to Chicago

Direct flights from Raleigh to Chicago

Last-minute flights going from Raleigh to Chicago

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

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

Recent fares are near the typical level

April, February, and August offer the lowest median prices

Direct flights average 2h 30m

Connecting flights are dominant on this route

Frontier Airlines offers a deal for $207

Deals appear frequently on this route

Raleigh main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 06

Oct 07

Oct 07

Oct 13

Sep 11

Oct 25

Oct 14

Oct 27

Dec 21

Oct 31

Nov 03

Oct 07

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Raleigh to Chicago?

What's a cheap fare from Raleigh to Chicago?

What's the cheapest month to fly from Raleigh to Chicago?