$145 Cheap Flights from Redding (RDD) to Chicago (ORD)

View $145 flight on Tue, Jan 20, 2026Opens in a new window

Popular airlines from Redding, CA (RDD-Redding Municipal) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Redding to Chicago (RDD-ORD)

Prices were available within the past 7 days and start at $145 for one-way flights and $275 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Mon, Nov 3 - Wed, Nov 12
RDD
Redding
ORD
Chicago
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Mon, Nov 3 from Redding to Chicago, returning Wed, Nov 12, priced at $275 found 4 days ago
Hawaiian Airlines
Mon, Nov 3 - Sat, Nov 8
RDD
Redding
ORD
Chicago
$289 Roundtrip, found 4 days ago
$289
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Mon, Nov 3 from Redding to Chicago, returning Sat, Nov 8, priced at $289 found 4 days ago
Alaska Airlines
Tue, Jan 27 - Wed, Jan 28
RDD
Redding
ORD
Chicago
$290 Roundtrip, found 6 days ago
$290
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Jan 27 from Redding to Chicago, returning Wed, Jan 28, priced at $290 found 6 days ago
Hawaiian Airlines
Thu, Jan 29 - Tue, Feb 3
RDD
Redding
ORD
Chicago
$304 Roundtrip, found 6 days ago
$304
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Thu, Jan 29 from Redding to Chicago, returning Tue, Feb 3, priced at $304 found 6 days ago
Alaska Airlines
Mon, Jan 26 - Wed, Jan 28
RDD
Redding
ORD
Chicago
$304 Roundtrip, found 6 days ago
$304
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Jan 26 from Redding to Chicago, returning Wed, Jan 28, priced at $304 found 6 days ago
Alaska Airlines
Wed, Oct 22 - Tue, Oct 28
RDD
Redding
ORD
Chicago
$308 Roundtrip, found 3 days ago
$308
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Oct 22 from Redding to Chicago, returning Tue, Oct 28, priced at $308 found 3 days ago
Hawaiian Airlines
Mon, Nov 3 - Fri, Nov 14
RDD
Redding
ORD
Chicago
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Mon, Nov 3 from Redding to Chicago, returning Fri, Nov 14, priced at $315 found 4 days ago
Hawaiian Airlines
Tue, Oct 28 - Fri, Oct 31
RDD
Redding
ORD
Chicago
$318 Roundtrip, found 4 days ago
$318
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, Oct 28 from Redding to Chicago, returning Fri, Oct 31, priced at $318 found 4 days ago
Hawaiian Airlines
Tue, Oct 21 - Fri, Oct 31
RDD
Redding
ORD
Chicago
$319 Roundtrip, found 18 hours ago
$319
Roundtrip
found 18 hours ago
Select Hawaiian Airlines flight, departing Tue, Oct 21 from Redding to Chicago, returning Fri, Oct 31, priced at $319 found 18 hours ago
United
Fri, Oct 31 - Mon, Nov 3
RDD
Redding
ORD
Chicago
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select United flight, departing Fri, Oct 31 from Redding to Chicago, returning Mon, Nov 3, priced at $358 found 1 day ago

Find the cheapest month to fly from Redding (RDD) to Chicago (ORD)

August is typically the cheapest month to fly

From $284 - $798 per traveler.

Frequently asked questions

How much does a flight from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $145 or cheap return flight from $275 from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD)?
November is the least expensive month to fly from RDD to ORD. Avoiding peak travel times is often the key to scoring lower fares.
What is the cheapest airline that flies from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest RDD to ORD flight.
How many flights per day from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD)?
There aren't any daily direct flights available from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from RDD to ORD?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on various factors, such as the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) on time, select a flight that takes off from Redding Municipal Airport (RDD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from RDD to ORD shortly before your trip is usually more expensive. But if you're flexible with your departure times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a RDD to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a RDD to ORD flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the stress out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then personalize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Redding Municipal Airport (RDD) to O'Hare Intl. Airport (ORD)?
If you reserved your RDD to ORD flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

Travel information

Travel information

Origin airport
Redding Municipal
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, Hawaiian Airlines, United
Roundtrip price
$275
Distance
1777 mi

Book with confidence

Book with confidence

Redding to Chicago Flights

The cheapest times to fly from Redding to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Redding to Chicago are during the month of November. You can find some of the cheapest flights from Redding to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Redding to Chicago

Sunday is one of the best days to book for cheap flights from Redding to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Redding to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Redding to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $145 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Redding to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Redding to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Redding to Chicago Flights

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*Available to One Key members.