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Cheap flights from Oakland, California to Chicago from $71

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Chicago departing on 11/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Oakland, California to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Oakland, California to Chicago.

Cheap last minute flights

Planning a quick getaway from Oakland, California to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Oakland, California to Chicago

Find recent round-trip train or bus tickets from Oakland, California to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:06 am - 11:25 pmOAK-ORD
11h 19m1 stop
10:13 pm - 9:26 amORD-OAK
13h 13m1 stop
$114Spirit Airlines
Find Deal
Wed, Nov 6 - Wed, Nov 13
7:58 pm - 4:45 amOAK-ORD
30h 47m2 stops
10:13 pm - 9:26 amORD-OAK
13h 13m1 stop
$140Spirit Airlines
Find Deal
Tue, Nov 12 - Thu, Nov 14
1:45 pm - 10:25 pmOAK-MDW
6h 40m1 stop
5:35 am - 11:30 amMDW-OAK
7h 55m1 stop
$208Southwest
Find Deal
Wed, Nov 13 - Sun, Nov 17
6:00 am - 3:40 pmOAK-MDW
7h 40m2 stops
7:00 am - 11:10 amMDW-OAK
6h 10m1 stop
$213Southwest
Find Deal
Tue, Nov 12 - Fri, Nov 15
2:36 pm - 11:59 pmOAK-ORD
7h 23m1 stop
3:35 pm - 8:49 amORD-OAK
19h 14m1 stop
$242Alaska Airlines
Find Deal
Mon, Jan 6 - Fri, Jan 10
12:50 pm - 10:03 pmOAK-ORD
7h 13m1 stop
7:20 am - 12:10 pmORD-OAK
6h 50m1 stop
$276Delta
Find Deal
Sat, Dec 7 - Tue, Dec 10
8:50 am - 4:59 pmOAK-ORD
30h 09m2 stops
5:34 pm - 6:49 pmORD-OAK
27h 15m2 stops
$292Alaska Airlines
Find Deal
Thu, Dec 5 - Thu, Dec 12
12:50 pm - 10:03 pmOAK-ORD
7h 13m1 stop
7:00 pm - 12:14 amORD-OAK
7h 14m1 stop
$317Delta
Find Deal
Mon, Dec 9 - Tue, Dec 10
5:59 pm - 8:45 amOAK-MDW
12h 46m1 stop
7:00 am - 9:15 pmMDW-OAK
16h 15m2 stops
$652Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
5:59 pm - 8:45 amOAK-MDW
12h 46m1 stop
6:05 am - 9:15 pmMDW-OAK
17h 10m2 stops
$751Frontier
Find Deal
Fri, Nov 15 - Mon, Nov 18
3:18 pm - 4:35 amOAK-ORD
11h 17m1 stop
$71Spirit Airlines
Find Deal
Mon, Nov 25
3:00 pm - 5:30 amOAK-ORD
12h 30m1 stop
$76Spirit Airlines
Find Deal
Tue, Dec 10
5:40 am - 11:45 amOAK-MDW
4h 05mnonstop
$95Southwest
Find Deal
Sun, Nov 17
4:50 pm - 12:50 amOAK-MDW
6h 00m1 stop
$100Southwest
Find Deal
Thu, Nov 14
2:36 pm - 11:59 pmOAK-ORD
7h 23m1 stop
$104Alaska Airlines
Find Deal
Thu, Jan 9
7:32 pm - 5:30 amOAK-ORD
7h 58m1 stop
$134Alaska Airlines
Find Deal
Wed, Jan 1
6:00 am - 5:02 pmOAK-MDW
9h 02m2 stops
$143Delta
Find Deal
Tue, Nov 19
5:01 pm - 9:32 amOAK-MDW
14h 31m2 stops
$214Delta
Find Deal
Mon, Nov 18
5:59 pm - 8:45 amOAK-MDW
12h 46m1 stop
$397Frontier
Find Deal
Wed, Nov 20
5:59 pm - 8:45 amOAK-MDW
12h 46m1 stop
$408Frontier
Find Deal
Mon, Nov 18
3:24 pm - 6:30 amOAK-ORD
13h 06m1 stop
11:08 pm - 9:06 amORD-OAK
11h 58m1 stop
$318Spirit Airlines
Find Deal
Thu, Oct 24 - Mon, Oct 28
5:19 am - 10:48 amOAK-ORD
27h 29m1 stop
5:19 pm - 11:59 pmORD-OAK
8h 40m1 stop
$321Spirit Airlines
Find Deal
Thu, Oct 24 - Tue, Oct 29
4:04 pm - 6:30 amOAK-ORD
12h 26m2 stops
11:08 pm - 9:06 amORD-OAK
11h 58m1 stop
$344Spirit Airlines
Find Deal
Thu, Oct 24 - Mon, Oct 28
10:55 pm - 9:59 amOAK-MDW
9h 04m1 stop
2:10 pm - 9:31 pmMDW-OAK
9h 21m1 stop
$508Delta
Find Deal
Fri, Oct 25 - Mon, Oct 28
12:50 pm - 9:44 pmOAK-ORD
6h 54m1 stop
1:40 pm - 9:36 pmORD-OAK
9h 56m1 stop
$508Delta
Find Deal
Thu, Oct 24 - Fri, Oct 25
2:29 pm - 11:59 pmOAK-ORD
7h 30m1 stop
6:20 am - 1:47 pmORD-OAK
9h 27m1 stop
$563Alaska Airlines
Find Deal
Thu, Oct 24 - Mon, Oct 28
1:05 pm - 7:10 pmOAK-MDW
4h 05mnonstop
7:35 pm - 10:05 pmMDW-OAK
4h 30mnonstop
$600Southwest
Find Deal
Thu, Oct 24 - Mon, Oct 28
6:00 am - 1:50 pmOAK-MDW
5h 50m1 stop
8:20 am - 10:55 amMDW-OAK
4h 35mnonstop
$605Southwest
Find Deal
Thu, Oct 24 - Mon, Oct 28
2:29 pm - 11:59 pmOAK-ORD
7h 30m1 stop
7:00 am - 11:48 pmORD-OAK
18h 48m2 stops
$716Alaska Airlines
Find Deal
Thu, Oct 24 - Mon, Oct 28
11:59 pm - 2:47 pmOAK-ORD
12h 48m1 stop
3:55 am - 4:59 pmORD-OAK
15h 04m1 stop
$974Frontier
Find Deal
Fri, Oct 25 - Sun, Oct 27
5:40 am - 11:45 amOAK-MDW
4h 05mnonstop
5:10 pm - 7:55 pmMDW-OAK
4h 45mnonstop
$224Southwest
Find Deal
Sun, Dec 8 - Wed, Dec 11
10:50 am - 4:55 pmOAK-MDW
4h 05mnonstop
5:35 pm - 8:20 pmMDW-OAK
4h 45mnonstop
$521Southwest
Find Deal
Wed, Nov 6 - Fri, Nov 8
10:25 am - 4:35 pmOAK-MDW
4h 10mnonstop
8:40 am - 11:25 amMDW-OAK
4h 45mnonstop
$594Southwest
Find Deal
Sat, Nov 2 - Sat, Nov 9
5:15 am - 11:20 amOAK-MDW
4h 05mnonstop
6:30 am - 9:20 amMDW-OAK
4h 50mnonstop
$744Southwest
Find Deal
Tue, Nov 26 - Sun, Dec 1
5:40 am - 11:45 amOAK-MDW
4h 05mnonstop
5:10 pm - 7:55 pmMDW-OAK
4h 45mnonstop
$757Southwest
Find Deal
Sat, Nov 30 - Wed, Dec 4

Spirit Airlines flights from Oakland, California to Chicago

Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Spirit Airlines
Nov 6
OAK10:06 amOakland
11h 19m
1 stop
ORD11:25 pmChicago O'Hare Intl
Nov 13
ORD10:13 pmChicago O'Hare Intl
13h 13m
1 stop
OAK9:26 amOakland
Spirit Airlines
Nov 12
OAK7:58 pmOakland
30h 47m
2 stops
ORD4:45 amChicago O'Hare Intl
Nov 14
ORD10:13 pmChicago O'Hare Intl
13h 13m
1 stop
OAK9:26 amOakland
Spirit Airlines
Nov 6
OAK10:06 amOakland
11h 19m
1 stop
ORD11:25 pmChicago O'Hare Intl
Nov 12
ORD10:13 pmChicago O'Hare Intl
18h 10m
1 stop
OAK2:23 pmOakland

Delta flights from Oakland, California to Chicago

Our best Delta deals on Oakland, California to Chicago flight tickets
Delta
Dec 7
OAK12:50 pmOakland
7h 13m
1 stop
ORD10:03 pmChicago O'Hare Intl
Dec 10
ORD7:20 amChicago O'Hare Intl
6h 50m
1 stop
OAK12:10 pmOakland
Delta
Dec 9
OAK12:50 pmOakland
7h 13m
1 stop
ORD10:03 pmChicago O'Hare Intl
Dec 10
ORD7:00 pmChicago O'Hare Intl
7h 14m
1 stop
OAK12:14 amOakland
Delta
Dec 17
OAK6:00 amOakland
8h 53m
2 stops
ORD4:53 pmChicago O'Hare Intl
Dec 19
ORD7:20 amChicago O'Hare Intl
6h 50m
1 stop
OAK12:10 pmOakland

How to get the cheapest flight ticket from Oakland, California to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Oakland, California to Chicago?

April. The cheapest time of year to fly to Chicago from Oakland, California is April. Most expensive is June

What is the cheapest day to depart Oakland, California for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Monday

When is the cheapest time to fly from Oakland, California to Chicago?

In the afternoon. Oakland, California to Chicago flights are approximately 24% more expensive in the evening than in the afternoon

What is the cheapest airline that flies to Chicago from Oakland, California?

Frontier. Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Oakland, California to Chicago

What is the cheapest Oakland, California to Chicago flight route?

Oakland - Chicago O'Hare Intl. Fly from Oakland to Chicago O'Hare Intl for the best Oakland, California - Chicago flight prices

How far in advance should you book Oakland, California to Chicago flights?

8 days before. The cheapest time to buy a flight from Oakland, California to Chicago is approximately 8 days to departure

How many flights depart from Oakland, California to Chicago on average per day?

3 flights are operational weekly from Oakland, California to Chicago as of October 2024. The most popular departure time for this route is 6:00AM, with 60% of flights per day taking off at noon.

How many flights depart from Oakland, California to Chicago on average per week?

As of October 2024, 25 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Sunday, with 16% of weekly flights taking off on this day.

Can stopping save me money on Oakland, California to Chicago flights?

You could potentially save up to 25% on your flight if you consider stops on a Oakland, California to Chicago flight.

How have Oakland, California to Chicago flight prices changed over time?

As of October 2024, prices for Oakland, California to Chicago flights are approximately 119% more expensive when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Oakland, California to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Oakland, California to Chicago (OAK to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago

Best Price Found

$71

Fastest flight time

4h 05m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Oakland, California in the past 72 hours is $71. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $114.
The fastest flight from Oakland, California to Chicago takes 4h 05m
Direct flights go from Oakland, California to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

  • How far is Oakland to Chicago by plane?

    The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 05m by plane in normal conditions.

  • When did momondo last update prices for flights from Oakland Airport to Chicago?

    Prices for flights from Oakland Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Oakland Airport to Chicago?

  • How old do you have to be to fly from Oakland Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Oakland, California to Chicago?

  • What is the most popular airline from Oakland, California to Chicago?


Best airlines flying from Oakland, California to Chicago

Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $79Free CancellationRating
6.1
3,618 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $141Free CancellationRating
6.3
8,200 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $158Free CancellationRating
8.0
9,416 reviews
Search Alaska Airlines flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,892 reviews
Search Delta flights
SouthwestPriceFrom $237Free CancellationRating
8.1
5,158 reviews
Search Southwest flights
  • Southwest Flights From Oakland, California to Chicago

    Across 25 Southwest flights from Oakland, California to Chicago this week, the average price was $383, with the best Southwest deals starting from $237 round-trip. 5,158 users have rated Southwest on momondo, with an average score of 8.1/10.


Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oakland.

Can I find flights from Oakland to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Oakland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Oakland to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Oakland.

I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Oakland to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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