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Flights from Oakland to Chicago

Oakland to Chicago Flight Information

The approximate distance between Oakland and Chicago is 2,969.56 km. Average flight time from Oakland to Chicago is around 5 hours 52 minutes. According to Trip.com data, travel demand hits its peak in July.

Cheapest one-way
US$86
Frontier Airlines Frontier Airlines OAK-CHI 14h 51m · 1 stop Wed, Sep 16
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Cheapest round-trip
US$288
Alaska Airlines Alaska Airlines OAK-CHI 8h 30m · 2 stops Thu, Aug 20 - Mon, Aug 24
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Recommended airlines
Frontier Airlines Frontier Airlines Cheapest · From US$86
When to fly
September
Cheapest
July
Peak season
Route details
2,969.56 km
Flight distance
5h 52m
Average flight time

Search cheap flights from Oakland to Chicago in the next 3 months. Based on Trip.com's latest 7-day data, one-way fares start at US$125, and round-trip tickets start at US$288.

      • OAK 13:29
        8h 30m
        1 stop
        ORD 23:59
        Oakland - Chicago | Thu, Aug 20 | Alaska Airlines
        ORD 06:01
        7h 5m
        1 stop
        OAK 11:06
        Chicago - Oakland | Mon, Aug 24 | Alaska Airlines
        US$288 US$607
        53% off
        53% off
        US$607 US$288
      • OAK 15:13
        6h 46m
        1 stop
        ORD 23:59
        Oakland - Chicago | Fri, Aug 21 | Alaska Airlines
        ORD 06:01
        7h 5m
        1 stop
        OAK 11:06
        Chicago - Oakland | Mon, Aug 24 | Alaska Airlines
        US$290 US$607
        52% off
        52% off
        US$607 US$290
      • OAK 15:13
        20h 9m
        1 stop
        ORD 13:22
        Oakland - Chicago | Sat, Sep 5 | Alaska Airlines
        ORD 07:20
        9h 13m
        1 stop
        OAK 14:33
        Chicago - Oakland | Tue, Sep 8 | Alaska Airlines
        US$292 US$607
        52% off
        52% off
        US$607 US$292
      • OAK 19:51
        8h 29m
        1 stop
        ORD 06:20
        Oakland - Chicago | Tue, Sep 1 | Alaska Airlines
        ORD 16:45
        7h 53m
        1 stop
        OAK 22:38
        Chicago - Oakland | Sat, Sep 5 | Delta Air Lines
        US$295
        51% off
        US$607 US$295
      • OAK 12:33
        7h
        1 stop
        ORD 21:33
        Oakland - Chicago | Sat, Sep 5 | Delta Air Lines
        ORD 07:20
        9h 13m
        1 stop
        OAK 14:33
        Chicago - Oakland | Tue, Sep 8 | Alaska Airlines
        US$296
        51% off
        US$607 US$296
      • OAK 13:29
        8h 30m
        1 stop
        ORD 23:59
        Oakland - Chicago | Thu, Sep 10 | Alaska Airlines
        ORD 06:00
        9h 19m
        1 stop
        OAK 13:19
        Chicago - Oakland | Tue, Sep 15 | Alaska Airlines
        US$296
        51% off
        US$607 US$296
      • OAK 14:15
        7h 44m
        1 stop
        ORD 23:59
        Oakland - Chicago | Wed, Sep 16 | Alaska Airlines
        ORD 14:18
        7h 34m
        1 stop
        OAK 19:52
        Chicago - Oakland | Sat, Sep 19 | Alaska Airlines
        US$298
        51% off
        US$607 US$298
      • OAK 13:00
        17h 25m
        1 stop
        CHI 14:00
        Oakland - Chicago | Wed, Aug 19 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        OAK 16:00
        Chicago - Oakland | Fri, Aug 21 | Normal Airline
        More cheap flights
        More cheap flights
      • Cheapest nonstop
        OAK 23:55
        4h
        Nonstop
        MDW 05:55
        Oakland - Chicago | Sun, Sep 6 | Hahn Air
        US$125 US$195
        36% off
        36% off
        US$195 US$125
      • OAK 12:47
        14h 51m
        1 stop
        ORD 05:38
        Oakland - Chicago | Wed, Sep 16 | Frontier Airlines
        US$86 US$195
        56% off
        56% off
        US$195 US$86
      • OAK 13:29
        8h 30m
        1 stop
        ORD 23:59
        Oakland - Chicago | Mon, Sep 14 | Alaska Airlines
        US$130 US$195
        33% off
        33% off
        US$195 US$130
      • OAK 13:29
        8h 30m
        1 stop
        ORD 23:59
        Oakland - Chicago | Mon, Aug 31 | Alaska Airlines
        US$130
        33% off
        US$195 US$130
      • OAK 15:14
        6h 45m
        1 stop
        ORD 23:59
        Oakland - Chicago | Thu, Oct 15 | Alaska Airlines
        US$130
        33% off
        US$195 US$130
      • OAK 15:13
        6h 46m
        1 stop
        ORD 23:59
        Oakland - Chicago | Sun, Sep 6 | Alaska Airlines
        US$140
        28% off
        US$195 US$140
      • OAK 13:00
        17h 25m
        1 stop
        CHI 14:00
        Oakland - Chicago | Wed, Aug 19 | Normal Airline
        More cheap flights
        More cheap flights

Frequently Asked Questions

  • What are the cheapest flights from Oakland to Chicago (OAK-CHI)?

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as US$86 on Cheapest nonstop routes (e.g. OAK to ORD on Wed, Sep 16), while Alaska Airlines offers Cheapest nonstop round-trips from US$288 departing on Thu, Aug 20 and returning on Mon, Aug 24.
  • It takes about 5 hours 52 minutes to fly from Oakland to Chicago.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Oakland to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Oakland to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Wed, Sep 16, with one-way flights priced at just US$86.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Hahn Air.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Oakland to Chicago is September, when demand for travel is lower.
  • After crunching the numbers on our August flight calendar, it's currently cheapest to fly from Oakland to Chicago on August 24, 2026 with Delta Air Lines, with prices starting at US$233.
  • You can land at any one of the following hubs in Chicago, with Oakland San Francisco Bay Airport to Chicago Midway International Airport (OAK-MDW) is by far the most common option on this route: Chicago Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Oakland is 2h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Oakland to Chicago is US$292. Fares vary by travel date, airline and availability.
  • Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Oakland to Chicago is US$596. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Oakland and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

Trip.com Airline Insights on Flights from Oakland to Chicago

Which airline offers the cheapest direct flights from Oakland to Chicago?

Data is based on the average price of all nonstop flights from Oakland to Chicago on Trip.com over the past 12 months.

Based on Trip.com’s data from the past 12 months, Alaska Airlines provides the lowest-priced direct flights from Oakland to Chicago, with fares starting at US$247.

US$219
US$247
US$276
US$304
US$332
Alaska Airlines
US$247
Alaska Airlines
Hawaiian Airlines
US$332
Hawaiian Airlines

How many flights fly from Oakland to Chicago daily?

The data is based on the flight numbers for each day of the week from Oakland to Chicago within the Trip.com database over the past month.

Based on the past month's historical data from Trip.com, the number of flights from Oakland to Chicago is the highest on Friday and the lowest on Saturday.

17
11
4
0
Highest
13
Mon
10
Tue
10
Wed
14
Thu
17
Fri
4
Sat
12
Sun

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Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.