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$338+ Cheap flights from Redding (RDD) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
RDD — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This Expedia deal was found by Cheapflights users on 5/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:17 pm
RDD
-
ORD
1 stop6h 42m
Alaska Airlines
Wed 6/106:00 am
ORD
-
RDD
1 stop10h 40m
Alaska Airlines
Deal found 5/6$338
This United Airlines deal was found by Cheapflights users on 5/9. 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.
Fri 7/37:55 pm
RDD
-
ORD
1 stop6h 56m
United Airlines
Tue 7/78:46 am
ORD
-
RDD
1 stop7h 40m
United Airlines
Deal found 5/9$348
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/273:17 pm
RDD
-
ORD
1 stop6h 42m
Alaska Airlines
Wed 6/37:40 am
ORD
-
RDD
1 stop8h 57m
Alaska Airlines
Deal found 5/8$378
This United Airlines deal was found by Cheapflights users on 5/7. 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.
Fri 6/57:55 pm
RDD
-
ORD
1 stop6h 56m
United Airlines
Thu 6/113:57 pm
ORD
-
RDD
1 stop10h 01m
United Airlines
Deal found 5/7$396
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:17 pm
RDD
-
ORD
1 stop6h 42m
Alaska Airlines
Sun 5/316:00 am
ORD
-
RDD
1 stop10h 37m
Alaska Airlines
Deal found 5/7$398
This United Airlines deal was found by Cheapflights users on 5/7. 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.
Fri 5/222:14 pm
RDD
-
ORD
1 stop8h 45m
United Airlines
Tue 5/267:00 am
ORD
-
RDD
1 stop7h 06m
United Airlines
Deal found 5/7$408
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:17 pm
RDD
-
ORD
1 stop6h 42m
Alaska Airlines
Wed 6/37:40 am
ORD
-
RDD
1 stop8h 57m
Alaska Airlines
Deal found 5/8$409
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Sun 6/77:55 pm
RDD
-
ORD
1 stop6h 56m
United Airlines
Sat 6/136:13 am
ORD
-
RDD
1 stop7h 33m
United Airlines
Deal found 5/8$420
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:17 pm
RDD
-
ORD
1 stop6h 42m
Alaska Airlines
Sun 5/317:40 am
ORD
-
RDD
1 stop8h 57m
Alaska Airlines
Deal found 5/6$449
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Sat 5/307:55 pm
RDD
-
ORD
1 stop6h 56m
United Airlines
Thu 6/46:13 am
ORD
-
RDD
1 stop7h 33m
United Airlines
Deal found 5/8$474
This United Airlines deal was found by Cheapflights users on 5/9. 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.
Fri 7/107:55 pm
RDD
-
ORD
1 stop6h 56m
United Airlines
Mon 7/133:57 pm
ORD
-
RDD
1 stop10h 01m
United Airlines
Deal found 5/9$476
This United Airlines deal was found by Cheapflights users on 5/9. 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.
Fri 5/297:55 pm
RDD
-
ORD
1 stop8h 37m
United Airlines
Sun 5/316:13 am
ORD
-
RDD
1 stop7h 33m
United Airlines
Deal found 5/9$478

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$338
(Expedia)
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)
Search Deals

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 May 10, 2026.
Use the filters below to find and compare flights from Redding to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 7/3

7:55 pm-4:51 am

1 stop6h 56m

Chicago O'Hare Intl

Tue 7/7

8:46 am-2:26 pm

1 stop7h 40m

$348

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 6/5

7:55 pm-4:51 am

1 stop6h 56m

Chicago O'Hare Intl

Thu 6/11

3:57 pm-11:58 pm

1 stop10h 01m

$396

ReddingChicago

RDD - ORD

RDDORD

Redding

Thu 5/28

3:17 pm-11:59 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 5/31

6:00 am-2:37 pm

1 stop10h 37m

$398
Quickest round-trip

ReddingChicago

RDD - ORD

RDDORD

Redding

Sun 6/7

7:55 pm-4:51 am

1 stop6h 56m

Chicago O'Hare Intl

Sat 6/13

6:13 am-11:46 am

1 stop7h 33m

$420

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 5/29

3:17 pm-11:59 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 5/31

7:40 am-2:37 pm

1 stop8h 57m

$449

ReddingChicago

RDD - ORD

RDDORD

Redding

Wed 6/3

3:17 pm-6:50 pm

2 stops25h 33m

Chicago O'Hare Intl

Wed 6/10

6:00 am-2:40 pm

1 stop10h 40m

$480

ReddingChicago

RDD - ORD

RDDORD

Redding

Thu 7/2

2:14 pm-12:59 am

1 stop8h 45m

Chicago O'Hare Intl

Mon 7/6

6:10 am-11:46 am

1 stop7h 36m

$483

ReddingChicago

RDD - ORD

RDDORD

Redding

Fri 7/3

7:55 pm-4:51 am

1 stop6h 56m

Chicago O'Hare Intl

Mon 7/6

6:10 am-11:46 am

1 stop7h 36m

$483

ReddingChicago

RDD - ORD

RDDORD

Redding

Thu 5/21

2:14 pm-12:59 am

1 stop8h 45m

Chicago O'Hare Intl

Mon 5/25

6:10 am-11:46 am

1 stop7h 36m

$484

ReddingChicago

RDD - ORD

RDDORD

Redding

Thu 5/28

6:11 pm-4:58 am

1 stop8h 47m

Chicago O'Hare Intl

Fri 6/5

3:57 pm-11:58 pm

1 stop10h 01m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 13 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Redding-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Redding-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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
No data available for this route at this time. Please check back soon.

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 May 10, 2026.
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
9,694 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

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
9,694 reviews
United Airlines
7.4
Good
9,694 reviews

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

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 42m. Fly via United Airlines or Alaska 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Redding to Chicago

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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$362Average$630FlexibilityNo cancel feeOn-time69%

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