Cheap flight deals from Oakland to Chicago

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

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

We monitor flight fares to help you find the best deals effortlessly

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  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Oakland (OAK) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Oakland to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Oakland (OAK) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around AED 1,575.

  • How long does it take to fly from Oakland (OAK) to Chicago (CHI)?

    It takes about 5 hours 37 minutes to fly from Oakland (OAK) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Oakland (OAK) to Chicago (CHI)?

    Airlines with flights from Oakland (OAK) to Chicago (CHI): Southwest Airlines.

  • What's the most popular airline for non-stop flights from Oakland (OAK) to Chicago (CHI)?

    Southwest Airlines operates 5 non-stop flights from Oakland (OAK) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Oakland to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Oakland to Chicago. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Oakland to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Oakland to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Mon, May 5 at AED 407 for one-way flights.
2
Compare cheap Oakland to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Oakland to Chicago. The cheapest airline operating is Southwest Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Oakland to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Oakland to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Oakland to Chicago to get exclusive deals for you.

Flight Info | Oakland to Chicago

Cheapest one-way flight price AED 271
Cheapest return ticket price AED 742
Off-season for travel April
Peak season for travel June
Flight distance 2,969.56 km
Average flight time 5 hours 37 minutes
Popular airline Alaska Airlines

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