Cheap flights from Oakland, California to Chicago from $85

Round-trip
1 adult
Economy
From?
To?
Mon 5/23
Mon 5/30

Deals available from 900+ travel sites.

Flight information for Oakland, California to Chicago
(OAK to CHI)

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

Best Price Found

$85

Fastest flight time

4h 04m

Direct flights

None

Airports in Chicago

3 airports
The best one-way flight to Chicago from Oakland, California in the past 72 hours is $85. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $183.
The fastest flight from Oakland, California to Chicago takes 4h 04m
There are no direct flights from Oakland, California to Chicago. Popular non-direct routes for this connection are Oakland Airport - Chicago O'Hare Intl Airport, Oakland Airport - Chicago Midway Airport and Oakland Airport - Chicago Greater Rockford Airport.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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?

August

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

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

Tuesday

The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

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

in the afternoon

Oakland, California to Chicago flights are approximately 21% more expensive at noon than in the afternoon

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

American Airlines

Alaska Airlines, American Airlines, and Delta 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?

52 days before

The cheapest time to buy a flight from Oakland, California to Chicago is approximately 52 days to departure

San Francisco Airport (SFO) to Chicago O'Hare Intl Airport (ORD)$270
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San Francisco Airport (SFO) to Chicago Midway Airport (MDW)$318
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Oakland Airport (OAK) to Chicago O'Hare Intl Airport (ORD)$173
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San Jose Airport (SJC) to Chicago O'Hare Intl Airport (ORD)$349
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Oakland Airport (OAK) to Chicago Midway Airport (MDW)$350
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San Jose Airport (SJC) to Chicago Midway Airport (MDW)$362
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If you are looking to fly from Oakland to Chicago, you are most likely going to fly from Oakland Airport to Chicago O'Hare Intl Airport, the most popular airports on that route. You may be looking for an airport near Oakland Airport to depart from when traveling to Chicago and luckily, there are options! You can try San Francisco Airport which is located in San Francisco, San Jose Airport which is located in San Jose, or Oakland Airport which is located in Oakland. You may be looking for an airport near Chicago O'Hare Intl Airport to land at when traveling from Oakland and luckily, there are options! You can try Chicago O'Hare Intl Airport which is located in Chicago, Chicago Midway Airport which is located in Chicago, or Chicago Greater Rockford Airport which is located in Chicago. The cheapest route from Oakland to Chicago is OAK — ORD with an average price of $173 RT during the month of May.


Easily compare round-trip flights from Oakland, California to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Oakland, California to Chicago by changing tabs
Spirit Airlines
Aug 27
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Aug 30
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland
Frontier
Jun 1
OAK4:21 amOakland
19h 38m
1 stop
MDW11:59 pmChicago Midway
Jun 8
MDW2:15 pmChicago Midway
15h 31m
1 stop
OAK5:46 amOakland
Multiple Airlines
Jun 1
OAK4:52 pmOakland
7h 07m
1 stop
MDW11:59 pmChicago Midway
Jun 8
MDW2:15 pmChicago Midway
15h 31m
1 stop
OAK5:46 amOakland
Delta
Oct 24
OAK5:55 pmOakland
9h 14m
1 stop
MDW3:09 amChicago Midway
Oct 28
MDW9:00 amChicago Midway
9h 08m
1 stop
OAK6:08 pmOakland
Spirit Airlines
Aug 17
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Aug 31
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland
Spirit Airlines
Aug 24
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Sep 7
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland

Find the cheapest one-way flights from Oakland, California to Chicago

If you're looking for one-way flights from Oakland, California to Chicago, view some of our deals below provided by Frontier and Spirit Airlines
Spirit Airlines
Aug 30
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Multiple Airlines
Jun 7
OAK7:02 amOakland
10h 56m
1 stop
ORD5:58 pmChicago O'Hare Intl
Frontier
Jun 6
OAK3:14 pmOakland
20h 35m
1 stop
MDW11:49 amChicago Midway

Search last-minute flights to Chicago from Oakland, California

Find and compare round-trip flight prices for your last-minute flight from Oakland, California to Chicago
Spirit Airlines
May 28
OAK1:25 amOakland
17h 26m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jun 6
ORD5:45 pmChicago O'Hare Intl
4h 35m
OAK10:20 pmOakland
Multiple Airlines
May 28
OAK1:25 amOakland
17h 26m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jul 1
ORD5:38 pmChicago O'Hare Intl
11h 58m
1 stop
OAK5:36 amOakland
Frontier
May 26
OAK4:21 amOakland
19h 35m
1 stop
MDW11:56 pmChicago Midway
May 31
MDW4:14 amChicago Midway
25h 21m
2 stops
OAK5:35 amOakland
Spirit Airlines
May 28
OAK1:25 amOakland
17h 26m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jun 4
ORD4:36 amChicago O'Hare Intl
10h 29m
1 stop
OAK3:05 pmOakland
Spirit Airlines
May 28
OAK1:25 amOakland
17h 26m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jul 2
ORD5:45 pmChicago O'Hare Intl
4h 35m
OAK10:20 pmOakland
Multiple Airlines
May 25
OAK3:12 pmOakland
38h 31m
2 stops
MDW5:43 amChicago Midway
May 29
MDW4:14 amChicago Midway
12h 23m
1 stop
OAK4:37 pmOakland

Best airlines flying from Oakland, California to Chicago

Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
AirlineRatingFree CancellationPrice
Spirit AirlinesPriceFrom $93Free CancellationRating
6.2
6.4

Boarding

5.8

Comfort

6.9

Crew

4.8

Entertainment

5.1

Food

Reviews

Horrible! I want a refund!!!!

1 / 10
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $107Free CancellationRating
8.0
8.3

Boarding

8.0

Comfort

8.5

Crew

7.4

Entertainment

7.3

Food

Reviews

Flight was delayed again. Crew was OK and informative but my sister in law's luggage was lost as was other passengers. Long travel day with MANY delays!!

1 / 10
Search Alaska Airlines flights
FrontierPriceFrom $111Free CancellationRating
6.1
6.4

Boarding

5.8

Comfort

7.0

Crew

4.7

Entertainment

5.0

Food

Reviews

Keep informed of flight delays and how long. Keeping track of bags better (lost bag and no one really cared)

1 / 10
Search Frontier flights
United AirlinesPriceFrom $155Free CancellationRating
7.4
7.7

Boarding

7.2

Comfort

8.0

Crew

6.9

Entertainment

6.6

Food

Reviews

It’s a hopper.

1 / 10
Search United Airlines flights
American AirlinesPriceFrom $177Free CancellationRating
7.4
7.8

Boarding

7.4

Comfort

8.2

Crew

7.1

Entertainment

6.6

Food

Reviews

Aside from the plane being filthy, it was a perfectly fine flight

1 / 10
Search American Airlines flights
DeltaPriceFrom $204Free CancellationRating
7.8
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

1 / 10
Search Delta flights

Spirit Airlines flights from Oakland, California to Chicago

Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Spirit Airlines
Aug 27
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Aug 30
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland
Spirit Airlines
Aug 17
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Aug 31
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland
Spirit Airlines
Aug 24
OAK3:00 amOakland
4h 04m
ORD7:04 amChicago O'Hare Intl
Sep 7
ORD5:21 pmChicago O'Hare Intl
4h 38m
OAK9:59 pmOakland

Frontier flights from Oakland, California to Chicago

Our best Frontier deals on Oakland, California to Chicago flight tickets
Frontier
Jun 1
OAK4:21 amOakland
19h 38m
1 stop
MDW11:59 pmChicago Midway
Jun 8
MDW2:15 pmChicago Midway
15h 31m
1 stop
OAK5:46 amOakland
Frontier
Jul 19
OAK8:06 amOakland
15h 56m
1 stop
MDW12:02 amChicago Midway
Aug 2
MDW2:39 pmChicago Midway
14h 57m
1 stop
OAK5:36 amOakland
Frontier
May 30
OAK1:42 pmOakland
22h 07m
1 stop
MDW11:49 amChicago Midway
Jun 6
MDW4:14 amChicago Midway
12h 15m
1 stop
OAK4:29 pmOakland

  • Are airlines flying from Oakland to Chicago offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Oakland to Chicago are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are Spirit Airlines, Delta, and United Airlines. You can search for the full list of airlines like Spirit Airlines that are offering this flexibility.

  • How far is Oakland to Chicago by plane?

    The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 04m by plane in normal conditions.



Alternative routes for Oakland, California to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Los Angeles to Chicago Flights
Fastest flight time3h 57m
Cheapest price$221
San Francisco to Chicago Flights
Fastest flight time4h 05m
Cheapest price$270
Santa Ana to Chicago Flights
Fastest flight time4h 01m
Cheapest price$291
San Diego to Chicago Flights
Fastest flight time3h 58m
Cheapest price$195
San Jose to Chicago Flights
Fastest flight time4h 08m
Cheapest price$349
Burbank to Chicago Flights
Fastest flight time5h 32m
Cheapest price$282
Los Angeles to St. Louis Flights
Fastest flight time3h 37m
Cheapest price$197
Sacramento to Chicago Flights
Fastest flight time3h 53m
Cheapest price$272
Ontario to Chicago Flights
Fastest flight time3h 46m
Cheapest price$348
Long Beach to Chicago Flights
Fastest flight time5h 48m
Cheapest price$336
San Francisco to St. Louis Flights
Fastest flight time6h 58m
Cheapest price$225
Ontario to St. Louis Flights
Fastest flight time4h 55m
Cheapest price$228

Why use momondo?

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.

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.

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.

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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