$30 Cheap flight deals from Raleigh (RDU) to Oak Brook (CHI)

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This Weekend's Flight Deals from Raleigh to Oak Brook

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jan 11 - Wed, Jan 28
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$239 Roundtrip, found 12 hours ago
$239
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from Raleigh - Durham Intl. to Midway Intl., returning Wed, Jan 28, priced at $239 found 12 hours ago
Sat, Jan 10 - Mon, Jan 12
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$301 Roundtrip, found 2 hours ago
$301
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, Jan 10 from Raleigh - Durham Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $301 found 2 hours ago

Airfares from $30 One Way, $94 Round Trip from Raleigh to Oak Brook

Prices starting at $94 for return flights and $30 for one-way flights to Oak Brook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Mar 19 - Thu, Mar 26
RDU
Raleigh
ORD
Chicago
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Mar 19 from Raleigh to Chicago, returning Thu, Mar 26, priced at $94 found 1 day ago
Fri, Feb 27 - Mon, Mar 2
RDU
Raleigh
ORD
Chicago
$101 Roundtrip, found 5 hours ago
$101
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Raleigh to Chicago, returning Mon, Mar 2, priced at $101 found 5 hours ago
Wed, Jan 28 - Wed, Feb 4
RDU
Raleigh
MDW
Chicago
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jan 28 from Raleigh to Chicago, returning Wed, Feb 4, priced at $128 found 2 days ago
Fri, Feb 27 - Fri, Mar 6
RDU
Raleigh
ORD
Chicago
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Feb 27 from Raleigh to Chicago, returning Fri, Mar 6, priced at $161 found 2 days ago
Thu, Mar 5 - Tue, Mar 31
RDU
Raleigh
ORD
Chicago
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Mar 5 from Raleigh to Chicago, returning Tue, Mar 31, priced at $171 found 4 hours ago

Oak Brook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 12 - Feb 15

3 night stay

Raleigh (RDU) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Raleigh (RDU)

American Airlines • Non-stop • Coach
Price was $677, price is now $486 per person
$486
per person
found 18 hours ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 12 - Feb 15

3 night stay

Raleigh (RDU) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Raleigh (RDU)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,078, price is now $816 per person
$816
per person
found 16 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

4BR Corporate Suite Central and Modern
2.0-star property

4BR Corporate Suite Central and Modern

10/10 Exceptional! (8 reviews)

Feb 19 - Feb 22

3 night stay

Raleigh (RDU) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $930, price is now $726 per person
$726
per person
found 6 hours ago
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More About Flying To Oak Brook from Raleigh

Route Information for Flights from Raleigh to Oak Brook

Origin Airport IATA Code
RDU
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Raleigh to Oak Brook

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.