Are there direct flights from Raleigh to Chicago?

Direct flights from Raleigh to Chicago are available, making up 17% of the observed flights in the trailing 90 days. For flights that include one or more stops, travelers typically experience two stopovers. This indicates that while direct options exist, a significant portion of routes involve connections.

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. For flights with one stop, the median flight time increases 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?

Historically, cheap flights from Raleigh to Chicago come up frequently. This route is classified as having frequent deals across the trailing 30 days. Travelers can often find favorable prices for this destination.

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 6 days ago

402 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 19, 2026.)

Today’s best flight deals from Raleigh to Chicago

Explore current cheapest deals departing from Raleigh to Chicago

Round trip

Sort by: Cheapest

October 3 - October 5

Cheapest

Best

RDU - Chicago

$339

$155

Round trip

August 5 - August 14

Earliest

RDU - Chicago

$243

$158

Round trip

October 5 - November 4

RDU - Chicago

$191

$158

Round trip

August 15 - August 24

RDU - Chicago

$242

$159

Round trip

October 5 - October 17

RDU - Chicago

$198

$160

Round trip

September 17 - October 17

RDU - Chicago

$184

$160

Round trip

October 22 - October 28

RDU - Chicago

$236

$166

Round trip

October 22 - October 24

RDU - Chicago

$244

$166

Round trip

September 10 - September 13

RDU - Chicago

$223

$168

Round trip

September 17 - October 15

RDU - Chicago

$184

$168

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

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 for flights from Raleigh to Chicago appear almost daily, offering frequent opportunities to find better prices.

When is the cheapest time to fly from Raleigh to Chicago? Historically, the cheapest month to fly is April, with a median fare of $139. Other affordable months include February, where the median fare is $159, and August, with a median fare of $164. These months offer the best chances for finding cheap flights from Raleigh to Chicago.

A typical journey from Raleigh to Chicago takes about 2h 30m. However, this route is characterized by a high proportion of connecting flights. Most itineraries connect at least once, with the median connecting journey taking 10h 29m and typically involving 2 stopovers. Only 17% of recent fares are for direct flights from Raleigh to Chicago, meaning you will likely have a layover.

The distance between Raleigh and Chicago is 1016 kilometers. This makes it a short-haul route, meaning flights are generally quicker and more frequent compared to longer international journeys.

How much is a round trip from Raleigh to Chicago

Regular price: $256 - $356

Prices are currently below the regular range.

The regular price range for flights from Raleigh to Chicago is $256 to $356. The current lowest deal is $155 with Frontier Airlines, for travel from Oct 3-Oct 5.

now $155

Low $256

High $356

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

American Airlines

Last-minute flights going from Raleigh to Chicago

Tue, Jul 21

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$415

$294

One-way

Wed, Jul 22

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

Frontier Airlines

$409

$294

One-way

Tue, Aug 4

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$265

$176

One-way

Tue, Aug 4

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (MDW)

$284

$207

One-way

Wed, Aug 5

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$244

$158

One-way

Wed, Aug 5

⌛ Last-Minute

RDU - Chicago

Raleigh (RDU) - Chicago (ORD)

Frontier Airlines

$263

$175

One-way

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

2 nights

Oct 3 - Oct 5

$339 → $155

54%

8 nights

Oct 27 - Nov 4

$335 → $170

49%

5 nights

Oct 4 - Oct 9

$337 → $192

43%

1 night

Aug 5 - Aug 6

$315 → $176

44%

Popular Airports to fly from Raleigh to Chicago

Raleigh - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Raleigh to Chicago are above the typical level for this 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 average 2h 30m

Direct flights to Chicago typically take 2h 30m, while connecting flights average 10h 29m.

✈️ Airlines & availability

Connecting flights are dominant

Only 17% of recent flights from Raleigh to Chicago are direct, with most having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers a deal at $155

Frontier Airlines has a deal for $155 from Raleigh-Durham International to Chicago Midway International.

🎯 Booking tip

Deals appear frequently

Deals on flights from Raleigh to Chicago are frequent, appearing often over 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 arrival in Chicago.

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

💸 Flights from ~$154

Chicago Midway International (MDW)

Chicago Midway International Airport provides a convenient arrival point closer to downtown Chicago.

📍 ~14 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$155

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative option for reaching the wider Chicago area.

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

💸 Flights from ~$211

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$216

Gerald R. Ford International (GRR)

Gerald R. Ford International offers a robust domestic network with a strong presence of both legacy and low-cost airlines.

📍 ~260 km from Chicago (reachable by car)

💸 Flights from ~$195

Dane County Regional (MSN)

Cheapest

Dane County Regional is a reliable regional hub with efficient operations and good amenities, offering direct highway access.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$138

South Bend International (SBN)

South Bend International is geographically the closest alternative airport to the Chicago metro area with convenient rail access.

📍 ~130 km from Chicago (reachable by train or car)

💸 Flights from ~$169

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for travelers heading to eastern domestic destinations.

📍 ~260 km from Chicago (reachable by car)

💸 Flights from ~$222

Business & First Class Flight Deals to Chicago

Elite

Jul 13

Chicago, United States

45% AI deal score

Chicago, United States

45% AI deal score

$2,363

From RDU

Elite

Aug 29

Chicago, United States

45% AI deal score

$2,377

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 observed was $226. Booking within 0-6 days of departure typically sees prices rise significantly, averaging around $485. Even booking 60+ days out tends to be more expensive, with an average price of $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 was $288. Fares can go significantly higher, with 75% of prices observed being $532 or less.

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

Related routes

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