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$140+ Cheap flights from Redding (RDD) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
RDD — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Redding to Chicago

Cheapest flights from Redding to Chicago
Explore the most affordable flight options available from Redding to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 pmRDD - ORD
1 stop16h 41mUnited Airlines
Sun 1/49:40 pmORD - RDD
2 stops19h 38mUnited Airlines
Deal found 12/16$665

Find flight deals from Redding to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Redding (RDD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$316
(Alaska Airlines)

One-way from

$140
(Kiwi.com)
Provider with most accurate pricing for Redding-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Redding-Chicago (CHI) flights.
Search Deals
From Redding to Chicago (CHI)
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One-way flight from Redding to Chicago (CHI)
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Redding to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Redding to Chicago that are best for you.

Fly from

Redding

Fly to

Chicago

Route

Depart

Return

Price

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 1/23

3:15 pm-11:50 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 1/27

6:06 pm-2:35 pm

1 stop22h 29m

$316

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 1/23

2:09 pm-11:14 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 1/27

7:00 am-8:53 pm

2 stops15h 53m

$495

ReddingChicago

RDD - ORD

RDDORD

Redding

Thu 1/1

6:28 pm-6:29 am

1 stop10h 01m

Chicago O'Hare Intl

Mon 1/5

6:08 pm-5:44 pm

1 stop25h 36m

$570

ReddingChicago

RDD - ORD

RDDORD

Redding

Wed 12/31

6:45 pm-1:26 pm

1 stop16h 41m

Chicago O'Hare Intl

Sun 1/4

9:40 pm-3:18 pm

2 stops19h 38m

$665

ReddingChicago

RDD - ORD

RDDORD

Redding

Wed 1/28

3:15 pm-11:50 pm

1 stop6h 35m

$140

ReddingChicago

RDD - ORD

RDDORD

Redding

Tue 12/30

1:00 pm-11:00 pm

1 stop8h 00m

$264

ReddingChicago

RDD - ORD

RDDORD

Redding

Wed 1/28

3:15 pm-10:46 pm

3 stops29h 31m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Compare providers for flights from Redding to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Redding to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Redding-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Redding-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Redding-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Redding-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Redding-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Redding to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Redding with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Redding to Chicago?

Currently, November is the cheapest month in which you can book a flight from Redding to Chicago (average of $274). Flying from Redding to Chicago in October is currently the most expensive (average of $674). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with United Airlines from Redding to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,091 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Redding to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Redding to Chicago?

    Most people fly from Redding (RDD) if they book a flight from Redding to Chicago. On average, Redding has 0 outbound flights to Chicago per day from 1 airline. Redding is conveniently located just 7.4 mi from Redding’s city center.

  • How long is the flight from Redding to Chicago?

    There are many flights that can get you from Redding to Chicago in 6h 35m. Fly via Alaska Airlines or United Airlines to get the fastest option. There are 1776 mi between Redding and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Redding to Chicago that include hotel bookings?

    Yes. In addition to deals on Redding to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Redding to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Redding to Chicago.

  • Can I find deals for business class flights from Redding to Chicago?

    Yes. Cheapflights offers flight deals from Redding to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Redding to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Redding to Chicago (average of $274). Flying from Redding to Chicago in October is currently the most expensive (average of $674). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
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Top airline flying from Redding to Chicago

Discover the top airline that operate flights from Redding to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$362Average$564FlexibilityNo cancel feeOn-time69%

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