RDD - ORD

$284 Find Cheap Flights from Redding to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Redding to Chicago departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$562
Alaska Airlines
Tue 10/27Sat 10/31
RDD - ORD • 1 stop
Cheapest one-way
$284
United Airlines
Mon 8/31
RDD - ORD • 1 stop
Top airlines
Cheapest • from $562 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Redding and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $419 (round-trip)
Shortest trip • 6h 30m (one-way)
Insights
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Flight Deals

Cheap Flights from Redding to Chicago (RDD-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Redding to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Redding to Chicago

Tue, Oct 27 - Sat, Oct 31
Alaska Airlines Logo
3:33 pm - 4:50 pm
RDD
-
ORD
23h 17m
1 stop
Alaska Airlines Logo
9:00 am - 2:53 pm
ORD
-
RDD
7h 53m
1 stop
$562Alaska Airlines
Tue, Nov 3 - Sun, Nov 8
Alaska Airlines Logo
3:23 pm - 5:40 am
RDD
-
ORD
12h 17m
1 stop
Alaska Airlines Logo
7:00 am - 2:43 pm
ORD
-
RDD
9h 43m
1 stop
$565Alaska Airlines
Wed, Sep 16 - Mon, Sep 21
Alaska Airlines Logo
3:54 pm - 12:07 pm
RDD
-
ORD
18h 13m
1 stop
Alaska Airlines Logo
6:00 am - 3:14 pm
ORD
-
RDD
11h 14m
1 stop
$568Alaska Airlines
Wed, Sep 16 - Mon, Sep 21
Alaska Airlines Logo
3:54 pm - 1:22 pm
RDD
-
ORD
19h 28m
2 stops
Alaska Airlines Logo
6:00 am - 3:14 pm
ORD
-
RDD
11h 14m
1 stop
$571Alaska Airlines
Wed, Sep 16 - Mon, Sep 21
Alaska Airlines Logo
3:54 pm - 1:22 pm
RDD
-
ORD
19h 28m
2 stops
Alaska Airlines Logo
2:18 pm - 3:14 pm
ORD
-
RDD
26h 56m
2 stops
$576Alaska Airlines
Tue, Oct 27 - Sat, Oct 31
United Airlines Logo
6:20 pm - 7:13 am
RDD
-
ORD
10h 53m
1 stop
United Airlines Logo
10:26 am - 11:45 pm
ORD
-
RDD
15h 19m
2 stops
$600United Airlines
Tue, Oct 27 - Sat, Oct 31
United Airlines Logo
7:15 am - 10:44 pm
RDD
-
ORD
13h 29m
2 stops
United Airlines Logo
10:26 am - 11:45 pm
ORD
-
RDD
15h 19m
2 stops
$634United Airlines
Tue, Nov 3 - Sun, Nov 8
United Airlines Logo
2:06 pm - 5:47 am
RDD
-
ORD
13h 41m
1 stop
United Airlines Logo
6:00 am - 11:32 am
ORD
-
RDD
7h 32m
1 stop
$646United Airlines
Thu, Sep 17 - Mon, Sep 21
United Airlines Logo
6:20 pm - 5:59 am
RDD
-
ORD
9h 39m
1 stop
United Airlines Logo
10:00 pm - 9:23 am
ORD
-
RDD
13h 23m
1 stop
$650United Airlines
Tue, Nov 3 - Sun, Nov 8
Alaska Airlines Logo
3:23 pm - 7:00 pm
RDD
-
ORD
25h 37m
2 stops
Alaska Airlines Logo
7:25 am - 2:43 pm
ORD
-
RDD
33h 18m
2 stops
$651Alaska Airlines
Booking Insights

KAYAK's insights & trends for Redding to Chicago flights

Get data-powered insights and trends into flights from Redding to Chicago to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Redding to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Redding to Chicago were found on Alaska Airlines ($562) and United Airlines ($600).

Good to know

Cheapest flight$284
Flight from Redding to Chicago

When to book flights from Redding to Chicago

Are your dates flexible? Find out the best times to travel from Redding to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Redding to Chicago flights

  • What is the cheapest flight from Redding to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Redding to Chicago O'Hare Intl Airport was $284 for a one-way ticket and $562 for a round-trip.

  • Do I need a passport to fly between Redding and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Redding to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Redding to Chicago?

    Star Alliance is the only airline alliance operating flights between Redding and Chicago.

  • How does KAYAK find such low prices on flights from Redding to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Redding to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Redding to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Redding is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Redding to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Redding with another airline. Booking your flights between Redding and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Redding to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Redding up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Redding to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Redding to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Redding to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9927 reviews
7.3Comfort
6.7Food
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

8.0 ExcellentDarly, Feb 2026
LAX - ORD
Read more United Airlines reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

Everything you need to know for your flight from Redding to Chicago

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