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Cheap flights Chicago — Oakland

Chicago (MDW, US) Oakland (OAK, US)
from $154 2 972 km ~4h 12 flights found 3 airlines cheapest on Thursday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $154 on 23.12.2026
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 33 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
24 Dec 2026, Thu
Southwest Airlines WN 2990
06:25
MDW Chicago Midway International Airport
11:20
OAK Metropolitan Oakland International Airport
4h 55m Direct
Tickets
$154
View this ticket
02 Dec 2026, Wed
Frontier Airlines F9 2999
19:21
MDW Chicago Midway International Airport
03:13
SFO San Francisco International Airport
7h 52m 2 stops
Kupi.com
$168
View this ticket
03 Dec 2026, Thu
Southwest Airlines WN 1536
06:05
MDW Chicago Midway International Airport
10:55
SFO San Francisco International Airport
4h 50m Direct
City.Travel
$171
View this ticket
15 Jan 2027, Fri
Southwest Airlines WN 1191
04:55
MDW Chicago Midway International Airport
09:40
OAK Metropolitan Oakland International Airport
4h 45m Direct
City.Travel
$171
View this ticket
28 Dec 2026, Mon
Frontier Airlines F9 2144
22:11
MDW Chicago Midway International Airport
06:37
OAK Metropolitan Oakland International Airport
8h 26m 2 stops
Kiwi.com
$241
View this ticket
17 Nov 2026, Tue
Allegiant Air G4 1423
01:31
MDW Chicago Midway International Airport
08:57
OAK Metropolitan Oakland International Airport
7h 26m 2 stops
Kiwi.com
$256
View this ticket
Route characteristics
Distance
2 972 km
Flight time
4h
Time difference
-2h
Minimum price
from $154 (23.12.2026)
Average price
$185
Maximum price
$333
Departures per week
1
Cheapest day
Thursday
Departure airports (1)
MDW Chicago Midway International Airport
Arrival airports (2)
OAK Metropolitan Oakland International Airport SFO San Francisco International Airport
Airlines (3)
WN Southwest Airlines F9 Frontier Airlines G4 Allegiant Air
Agencies (5)
Tickets Kupi.com City.Travel Kiwi.com Farera
Prices by day of week
Monday
$241
avg $241
Tuesday
$256
avg $256
Wednesday
$168
avg $168
Thursday
$154
avg $163
Cheapest
Friday
$171
avg $171
Price trend by month
November 2026
from $256
avg $256
1 flights
December 2026
from $154
avg $184
4 flights
January 2027
from $171
avg $171
1 flights
Airlines — cheapest prices 3
Southwest Airlines
Southwest Airlines
Low-cost 9 flights · 8 days
$154
Frontier Airlines
Frontier Airlines
Low-cost 2 flights · 2 days
$168
Allegiant Air
Allegiant Air
Low-cost 1 flights · 1 days
$256
Where to buy tickets 5
Tickets
1 tickets · 1 days
from $154
Kupi.com
1 tickets · 1 days
from $168
City.Travel
2 tickets · 2 days
from $171
Kiwi.com
2 tickets · 2 days
from $241
Farera
6 tickets · 5 days
from $265
Airports

From — Chicago (1)

  • MDW Chicago Midway International Airport

To — Oakland (2)

  • OAK Metropolitan Oakland International Airport
  • SFO San Francisco International Airport
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Frequently asked questions about the route Chicago — Oakland
How long is the flight from Chicago to Oakland?
Approximate flight time — 4h. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Chicago to Oakland?
The straight-line distance — 2 972 km.
How much do flights from Chicago to Oakland cost?
The minimum price over 3 months — from $154 on 23.12.2026.
What is the average ticket price?
The average price — $185. Range: $154 — $333.
What is the time difference between Chicago and Oakland?
The difference — -2h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport).
To which airports in Oakland do flights arrive?
To Oakland: OAK (Metropolitan Oakland International Airport), SFO (San Francisco International Airport).
Which airlines fly this route?
This route is served by 3 airlines: Southwest Airlines, Frontier Airlines, Allegiant Air.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $154. Total direct flights found: 3.
Which day of the week is cheapest?
The cheapest day of the week — Thursday.
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 Chicago — Oakland

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

From Chicago (MDW) flights depart from 1 airport: MDW. To Oakland (OAK) — 2 arrival airports: OAK, SFO.

3 airlines operate on this route: Southwest Airlines, Frontier Airlines, Allegiant Air.

The minimum price for the next 3 months — from $154 (23.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $185, ranging from $154 to $333. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Thursday.

Other destinations in United States from Chicago
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US
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US
Pittsburgh
US
Phoenix
US
Philadelphia
US
Portland
US
Norfolk
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New Orleans
US

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