Are there direct flights from Raleigh to Chicago?

Yes, direct flights from Raleigh to Chicago are available. Historically, approximately 9.8% of all flights on this route have been direct. For flights with connections, travelers typically experience a median of 2 stopovers.

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 24 minutes. For flights that include one stop, the median travel time increases to 8 hours and 19 minutes. The flight covers an approximate distance of 1016 kilometers.

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

Cheap flights from Raleigh to Chicago are a regular occurrence. This route is consistently observed to have competitive pricing. Travelers can typically find favorable deals with some regularity across the trailing 30 days.

Flights From Raleigh

To Chicago

Cheap Flights from Raleigh to Chicago

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Deals from

Raleigh

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

Prices updated 4 days ago

481 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 20, 2026.)

Today’s best flight deals from Raleigh to Chicago

Explore current cheapest deals departing from Raleigh to Chicago

2026-12-02 – 2026-12-05
RDU - Chicago
76% AI deal score
$295
$157
Round trip
2026-12-02 – 2026-12-12
RDU - Chicago
73% AI deal score
$250
$157
Round trip
2026-12-02 – 2026-12-08
RDU - Chicago
75% AI deal score
$279
$157
Round trip
2026-12-02 – 2026-12-09
RDU - Chicago
75% AI deal score
$279
$157
Round trip
2026-12-09 – 2026-12-12
RDU - Chicago
75% AI deal score
$294
$162
Round trip
2026-12-02 – 2026-12-03
RDU - Chicago
75% AI deal score
$297
$165
Round trip
2026-12-02 – 2026-12-10
RDU - Chicago
73% AI deal score
$264
$165
Round trip
2026-12-02 – 2026-12-14
RDU - Chicago
71% AI deal score
$244
$165
Round trip
2026-12-02 – 2026-12-11
RDU - Chicago
73% AI deal score
$261
$166
Round trip
2026-12-02 – 2026-12-07
RDU - Chicago
74% AI deal score
$289
$166
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 for cheap flights from Raleigh to Chicago are below the typical level, with prices typically ranging from $342–$759, and a median of $507. New deals for this route show up several times a week, indicating a regular cadence of price changes.

A typical journey from Raleigh to Chicago takes about 2h 29m. However, since most itineraries connect at least once, this median journey time often includes layovers. When you do connect, you can expect a typical journey with 2 stopovers.

The route from Raleigh to Chicago is considered a short-haul flight, covering a distance of 1016 kilometers.

When is the cheapest time to fly from Raleigh to Chicago? The data indicates that May is typically the most affordable month, with a median fare of $169. Other cost-effective options include August, with a median fare of $281, and January, where the median fare is $287.

How much is a round trip from Raleigh to Chicago

Regular price: $141 - $328

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

The regular price range for flights from Raleigh to Chicago is $141 to $328. The current lowest deal is $131 with Frontier Airlines, for travel from Nov 11-Dec 7.

now $131

Low $141

High $328

The cheapest time to fly from Raleigh to Chicago

The cheapest month to fly from RDU to CHI is May, with a median price of $169. The most expensive month is April, with a median price of $697. Prices are generally lower from January to September.

May

Cheapest

Flights from $169

April

Most Expensive

Flights from $697

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Raleigh to Chicago

United Airlines

Last-minute flights going from Raleigh to Chicago

Tue, Oct 20

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$617

$359

One-way

Tue, Oct 20

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$606

$367

One-way

Thu, Oct 22

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$593

$364

One-way

Thu, Oct 22

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$585

$373

One-way

Tue, Oct 27

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$432

$323

One-way

Thu, Nov 12

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$193

$186

One-way

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

2 nights

Oct 21 - Oct 23

$614 → $367

40%

2 nights

Oct 20 - Oct 22

$614 → $372

39%

2 nights

Oct 22 - Oct 24

$593 → $354

40%

1 night

Oct 22 - Oct 23

$596 → $375

37%

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Raleigh to Chicago are below the typical level at $131.

📅 Best time to fly

May, August, and January offer the lowest median prices

Historically, May ($169), August ($281), and January ($287) have offered the lowest median prices.

⏱️ Flight duration

Direct flights average 2h 29m

Direct flights to Chicago from Raleigh typically average 2h 29m, connecting flights average 22h 20m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, with 9.8% direct flights historically.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines offers direct flights from Raleigh to Chicago, with 1 direct deal recently.

🎯 Booking tip

Deals appear regularly

Deals on flights from Raleigh to Chicago appear regularly, with a median price of $168.

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 ~$163

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

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

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

💸 Flights from ~$174

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

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

💸 Flights from ~$316

Business & First Class Flight Deals to Chicago

50% AI deal score

$2,785

$2,287

Save $498

Air Canada, +1

Business Class

From RDU

Elite

Dec 09

Chicago, United States

49% AI deal score

$2,547

$2,210

Save $337

Air Canada, +1

Business Class

From RDU

Elite

Dec 03

Chicago, United States

49% AI deal score

$2,469

$2,278

Save $191

Alaska Airlines, Inc.

Business Class

From RDU

Elite

Dec 04

Chicago, United States

49% AI deal score

$2,541

$2,284

Save $257

Air Canada, +1

Business Class

From RDU

Elite

Dec 09

Chicago, United States

49% AI deal score

$2,803

$2,421

Save $382

Air Canada, +1

Business Class

From RDU

Elite

Dec 04

Chicago, United States

48% AI deal score

$2,530

$2,287

Save $243

Air Canada, +1

Business Class

From RDU

Elite

Dec 08

Chicago, United States

48% AI deal score

$2,483

$2,369

Save $114

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Raleigh to Chicago is typically 14-27 days before departure. During this period, the average price observed was around $627. Booking 60+ days out also presented a competitive average price of $660. Prices tend to increase significantly for very last-minute bookings, with flights booked 7-13 days prior averaging $1001.

A fare of $342 or less is considered a good price for flights from Raleigh to Chicago, based on pricing trends observed across the trailing quarter. Historically, the median price for this route has been $507. Fares exceeding $759 are typically in the higher price range for this route.

Historically, May has been the cheapest month to fly from Raleigh to Chicago, with a median price of $169. August and January also offered competitive prices, with median fares of $281 and $287 respectively. The annual median price for this route is $507, 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 is considered a short-haul flight, covering a distance of 1016 kilometers.

How much is a round trip from Raleigh to Chicago

Regular price: $141 - $328

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

The regular price range for flights from Raleigh to Chicago is $141 to $328. The current lowest deal is $131 with Frontier Airlines, for travel from Nov 11-Dec 7.

now $131

Low $141

High $328

The cheapest time to fly from Raleigh to Chicago

The cheapest month to fly from RDU to CHI is May, with a median price of $169. The most expensive month is April, with a median price of $697. Prices are generally lower from January to September.

May

Cheapest

Flights from $169

April

Most Expensive

Flights from $697

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Raleigh to Chicago

United Airlines

Last-minute flights going from Raleigh to Chicago

Tue, Oct 20

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$617

$359

One-way

Tue, Oct 20

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$606

$367

One-way

Thu, Oct 22

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$593

$364

One-way

Thu, Oct 22

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$585

$373

One-way

Tue, Oct 27

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$432

$323

One-way

Thu, Nov 12

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$193

$186

One-way

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

2 nights

Oct 21 - Oct 23

$614 → $367

40%

2 nights

Oct 20 - Oct 22

$614 → $372

39%

2 nights

Oct 22 - Oct 24

$593 → $354

40%

1 night

Oct 22 - Oct 23

$596 → $375

37%

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Raleigh to Chicago are below the typical level at $131.

📅 Best time to fly

May, August, and January offer the lowest median prices

Historically, May ($169), August ($281), and January ($287) have offered the lowest median prices.

⏱️ Flight duration

Direct flights average 2h 29m

Direct flights to Chicago from Raleigh typically average 2h 29m, connecting flights average 22h 20m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, with 9.8% direct flights historically.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines offers direct flights from Raleigh to Chicago, with 1 direct deal recently.

🎯 Booking tip

Deals appear regularly

Deals on flights from Raleigh to Chicago appear regularly, with a median price of $168.

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 ~$163

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

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

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

💸 Flights from ~$174

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

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

💸 Flights from ~$316

Chicago, United States

48% AI deal score

$2,483

$2,369

Save $114

Air Canada, +1

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 below the typical level

May, August, and January offer the lowest median prices

Direct flights average 2h 29m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

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

Dec 28

Nov 13

Nov 16

Oct 28

Nov 19

Dec 04

Dec 09

Dec 03

Dec 04

Dec 09

Dec 04

Dec 08

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 below the typical level

May, August, and January offer the lowest median prices

Direct flights average 2h 29m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

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

Dec 28

Nov 13

Nov 16

Oct 28

Nov 19

Dec 04

Dec 09

Dec 03

Dec 04

Dec 09

Dec 04

Dec 08

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?