Are there direct flights from Raleigh to Chicago?

Direct flights from Raleigh to Chicago are available, making up 17% of the total flights observed in the trailing 90 days. For flights that include stopovers, travelers typically experience a median of 2 connections. While direct options exist, a significant portion of routes involve at least one stop. Travelers should factor this into their planning when considering their journey.

How many hours is the flight from Raleigh to Chicago?

The typical direct flight from Raleigh to Chicago has a median duration of 2 hours and 30 minutes, covering a distance of 1016 kilometers. Flights with one stop, however, are significantly longer, with a median duration of 6 hours and 59 minutes. Travelers should consider whether the convenience of a direct flight outweighs the potential cost savings of a connecting flight, which can add several hours to the journey.

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

Historically, cheap flights from Raleigh to Chicago come up frequently. This route is classified as having frequent deals, indicating that opportunities for lower fares are regularly available. Travelers can often find competitive prices when planning their trips between these two cities. Consistent monitoring for deals is advisable for those seeking more economical travel options.

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 14 days ago

406 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 2026.)

Today’s best flight deals from Raleigh to Chicago

Explore current cheapest deals departing from Raleigh to Chicago

2026-09-08 – 2026-09-09
RDU - Chicago
73% AI deal score
$225
$146
Round trip
2026-08-31 – 2026-09-09
RDU - Chicago
75% AI deal score
$244
$146
Round trip
2026-08-31 – 2026-09-08
RDU - Chicago
75% AI deal score
$249
$148
Round trip
2026-09-09 – 2026-09-22
RDU - Chicago
49% AI deal score
$185
$151
Round trip
2026-09-09 – 2026-09-30
RDU - Chicago
48% AI deal score
$178
$151
Round trip
2026-08-31 – 2026-09-01
RDU - Chicago
77% AI deal score
$287
$151
Round trip
2026-09-08 – 2026-09-30
RDU - Chicago
48% AI deal score
$178
$151
Round trip
2026-09-08 – 2026-09-22
RDU - Chicago
49% AI deal score
$185
$151
Round trip
2026-08-31 – 2026-09-30
RDU - Chicago
71% AI deal score
$211
$151
Round trip
2026-08-31 – 2026-09-22
RDU - Chicago
71% AI deal score
$213
$151
Round trip

Raleigh to Chicago: Overview

Insights for flights from Raleigh to Chicago

Right now, only 1% of recent fares from Raleigh to Chicago are classified as a good price. Fares for this route typically range from $176–$532, with a median of $288. Current fares are significantly above the typical level, suggesting that prices are higher than usual for this route. New deals appear almost daily, so it is worth monitoring prices if you are looking for cheap flights from Raleigh to Chicago.

When considering the cheapest time to fly from Raleigh to Chicago, the data indicates that April is often the most affordable month, with a median fare of $139. Following closely, February also offers competitive prices, with a median fare of $159. August is another relatively inexpensive option, showing a median fare of $164.

A typical journey from Raleigh to Chicago takes about 2h 30m for direct flights. However, most itineraries connect at least once, with the median connecting journey taking 10h 29m. Only 17% of recent fares for this route are non-stop, meaning you will likely encounter at least 2 stopovers if you are not flying direct.

The distance between Raleigh and Chicago is 1016 kilometers. This classifies the route as a short-haul flight, indicating a relatively quick journey suitable for short trips or weekend getaways.

How much is a round trip from Raleigh to Chicago

Regular price: $239 - $328

Prices are currently below the regular range.

The regular price range for flights from Raleigh to Chicago is $239 to $328. The lowest deal found is $154 with Frontier Airlines, for travel from Aug 27-Aug 31.

now $154

Low $239

High $328

The cheapest time to fly from Raleigh to Chicago

Flights from RDU to CHI are cheapest in August, with a median price of $179. The most expensive month to fly 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

Mon, Aug 10

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$558

$316

One-way

Tue, Aug 11

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$436

$260

One-way

Tue, Aug 11

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$558

$295

One-way

Thu, Aug 13

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$533

$323

One-way

Thu, Aug 13

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$554

$332

One-way

Fri, Aug 14

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$493

$317

One-way

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

1 night

Aug 11 - Aug 12

$558 → $296

47%

3 nights

Aug 14 - Aug 17

$558 → $320

43%

4 nights

Aug 13 - Aug 17

$554 → $332

40%

1 night

Aug 12 - Aug 13

$537 → $323

40%

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares near the typical level

Recent fares from RDU to CHI are near the typical level for the route.

📅 Best time to fly

Fly in August for the best prices

Historically, August is the cheapest month to fly, with a median price of $179.

⏱️ Flight duration

Direct flights take 2h 30m

Direct flights to Chicago Midway International Airport typically take 2h 30m.

✈️ Airlines & availability

Connecting flights are common

Only 17% of recent flights from RDU to CHI are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a $154 deal

Frontier Airlines has a deal for $154 from RDU to CHI, departing August 27.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Raleigh to Chicago are frequent, appearing often in the last 30 days.

Raleigh main airports to depart from

Raleigh–Durham International (RDU)

Cheapest

Raleigh-Durham International Airport is a convenient departure point for flights from Raleigh to Chicago.

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

💸 Flights from ~$154

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$154

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)

💸 Flights from ~$222

Business & First Class Flight Deals to Chicago

73% AI deal score

$631

$507

Save $124

United Airlines

Business Class

From RDU

Elite

Aug 15

Chicago, United States

71% AI deal score

$1,008

$743

Save $265

From RDU

Elite

Oct 07

Chicago, United States

70% AI deal score

$667

$507

Save $160

From RDU

Elite

Nov 24

Chicago, United States

70% AI deal score

$968

$723

Save $245

From RDU

Chicago, United States

67% AI deal score

$3,359

$2,540

Save $819

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Aug 12

Chicago, United States

67% AI deal score

$3,418

$2,587

Save $831

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 between 28 and 59 days prior to departure. During this period, the average price for a flight is around $226. Booking within 7-13 days of travel sees prices rise to approximately $391, and waiting until 0-6 days before departure can result in an average price of $485. Planning ahead by at least one month can lead to more favorable fares.

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. Fares can go significantly higher, with 75% of prices observed being $532 or less. Aiming for a fare around $176 would put you in the lowest 25% of prices.

Historically, April has been the cheapest month to fly from Raleigh to Chicago, with a median price of $139. February and August also offer competitive fares, with median prices of $159 and $164 respectively. The annual median price for this route is $288, indicating that these months provide substantial savings. Travelers looking for lower prices should consider these months for their trips.

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 distance between Raleigh and Chicago is 1016 kilometers. This classifies the route as a short-haul flight, indicating a relatively quick journey suitable for short trips or weekend getaways.

How much is a round trip from Raleigh to Chicago

Regular price: $239 - $328

Prices are currently below the regular range.

The regular price range for flights from Raleigh to Chicago is $239 to $328. The lowest deal found is $154 with Frontier Airlines, for travel from Aug 27-Aug 31.

now $154

Low $239

High $328

The cheapest time to fly from Raleigh to Chicago

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

Mon, Aug 10

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$558

$316

One-way

Tue, Aug 11

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$436

$260

One-way

Tue, Aug 11

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$558

$295

One-way

Thu, Aug 13

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$533

$323

One-way

Thu, Aug 13

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$554

$332

One-way

Fri, Aug 14

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$493

$317

One-way

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

1 night

Aug 11 - Aug 12

$558 → $296

47%

3 nights

Aug 14 - Aug 17

$558 → $320

43%

4 nights

Aug 13 - Aug 17

$554 → $332

40%

1 night

Aug 12 - Aug 13

$537 → $323

40%

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares near the typical level

Recent fares from RDU to CHI are near the typical level for the route.

📅 Best time to fly

Fly in August for the best prices

Historically, August is the cheapest month to fly, with a median price of $179.

⏱️ Flight duration

Direct flights take 2h 30m

Direct flights to Chicago Midway International Airport typically take 2h 30m.

✈️ Airlines & availability

Connecting flights are common

Only 17% of recent flights from RDU to CHI are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a $154 deal

Frontier Airlines has a deal for $154 from RDU to CHI, departing August 27.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Raleigh to Chicago are frequent, appearing often in the last 30 days.

Raleigh main airports to depart from

Raleigh–Durham International (RDU)

Cheapest

Raleigh-Durham International Airport is a convenient departure point for flights from Raleigh to Chicago.

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

💸 Flights from ~$154

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$154

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)

💸 Flights from ~$222

Chicago, United States

73% AI deal score

$631

$507

Save $124

United Airlines

Business Class

From RDU

Elite

Aug 15

Chicago, United States

71% AI deal score

$1,008

$743

Save $265

From RDU

Elite

Oct 07

Chicago, United States

70% AI deal score

$667

$507

Save $160

From RDU

Elite

Nov 24

Chicago, United States

70% AI deal score

$968

$723

Save $245

From RDU

Chicago, United States

67% AI deal score

$3,418

$2,587

Save $831

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 near the typical level

Fly in August for the best prices

Direct flights take 2h 30m

Connecting flights are common

Frontier Airlines offers a $154 deal

Deals are frequent 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

Aug 17

Aug 17

Nov 10

Aug 15

Oct 07

Nov 24

Dec 11

Dec 30

Dec 23

Oct 29

Aug 12

Aug 12

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 near the typical level

Fly in August for the best prices

Direct flights take 2h 30m

Connecting flights are common

Frontier Airlines offers a $154 deal

Deals are frequent 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

Aug 17

Aug 17

Nov 10

Aug 15

Oct 07

Nov 24

Dec 11

Dec 30

Dec 23

Oct 29

Aug 12

Aug 12

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?