C Cityvator Cheap flights worldwide Part of Putivator
Flights Destinations Beaches Map Services Booking Collections Ratings
Home / Oakland — Chicago

Cheap flights Oakland — Chicago

Oakland (OAK, US) Chicago (MDW, US)
from $155 2 972 km ~4h 3 flights found 1 airlines cheapest on Friday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $155 on 27.11.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
Mo
Tu
We
Th
Fr
Sa
Su
December 2026
Mo
Tu
We
Th
Fr
Sa
Su
January 2027
Mo
Tu
We
Th
Fr
Sa
Su
Prices found for 3 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
27 Nov 2026, Fri
Southwest Airlines WN 2227
10:55
OAK Metropolitan Oakland International Airport
14:55
MDW Chicago Midway International Airport
4h Direct
Tickets
$155
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 3220
10:50
OAK Metropolitan Oakland International Airport
14:55
MDW Chicago Midway International Airport
4h 5m Direct
Farera
$270
View this ticket
Route characteristics
Distance
2 972 km
Flight time
4h
Time difference
+2h
Minimum price
from $155 (27.11.2026)
Average price
$232
Maximum price
$270
Cheapest day
Friday
Departure airports (1)
OAK Metropolitan Oakland International Airport
Arrival airports (1)
MDW Chicago Midway International Airport
Airlines (1)
WN Southwest Airlines
Agencies (2)
Tickets Farera
Prices by day of week
Friday
$155
avg $155
Cheapest
Sunday
$270
avg $270
Airlines — cheapest prices 1
Southwest Airlines
Southwest Airlines
Low-cost 3 flights · 3 days
$155
Where to buy tickets 2
Tickets
1 tickets · 1 days
from $155
Farera
2 tickets · 2 days
from $270
Airports

From — Oakland (1)

  • OAK Metropolitan Oakland International Airport

To — Chicago (1)

  • MDW Chicago Midway International Airport
Other destinations from Oakland
Albuquerque
US
Accra
GH
Arcata
US
Adler/Sochi
RU
Auckland
NZ
Almaty
KZ
Ahmedabad
IN
Amsterdam
NL · Hub
Anchorage
US
Ankara
TR
Aspen
US
Athens
GR
Frequently asked questions about the route Oakland — Chicago
How long is the flight from Oakland to Chicago?
Approximate flight time — 4h. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Oakland to Chicago?
The straight-line distance — 2 972 km.
How much do flights from Oakland to Chicago cost?
The minimum price over 3 months — from $155 on 27.11.2026.
What is the average ticket price?
The average price — $232. Range: $155 — $270.
What is the time difference between Oakland and Chicago?
The difference — +2h.
From which airports does Oakland operate flights?
From Oakland: OAK (Metropolitan Oakland International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport).
Which airlines fly this route?
This route is served by 1 airline: Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $155. Total direct flights found: 2.
Which day of the week is cheapest?
The cheapest day of the week — Friday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Oakland — Chicago

Flights Oakland — Chicago is a popular route. The straight-line distance is 2 972 km. Flight time 4h. Time difference +2h.

From Oakland (OAK) flights depart from 1 airport: OAK. To Chicago (MDW) — 1 arrival airport: MDW.

1 airline operate on this route: Southwest Airlines.

The minimum price for the next 3 months — from $155 (27.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $232, ranging from $155 to $270. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Friday.

Other destinations in United States from Oakland
Everett
US
Kahului
US
Ontario
US
Orlando
US
Owensboro
US
Page
US
Philadelphia
US
New York
US

Cheap flights worldwide. Search and compare prices from 1 159 airlines across 9 546 cities.

Flights

Flight search Destinations Beaches Map Services Booking Collections Ratings

Data

Open API for AI llms.txt ai.txt

Documents

Privacy Policy Terms of Use

Contacts

info@cityvator.com Part of Putivator
© 2026 Cityvator — flight search engine Data from open sources · Open API for AI