OAK to MDW

Oakland to Chicago flight ticket price

Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.

OAK
Oakland (OAK), United StatesMetropolitan Oak Intl
MDW
Chicago (MDW), United StatesMidway
Search

Live flights for Sat, 06 Jun 2026

Review fares, stops, timings and baggage. Use Search or View all flights for the complete search result.

Showing flight options for the selected travel date.
Currency: USD
Sat, 06 JunOAK to MDW$387 Sun, 07 JunOAK to MDW Mon, 08 JunOAK to MDW Tue, 09 JunOAK to MDW Wed, 10 JunOAK to MDW Thu, 11 JunOAK to MDW Fri, 12 JunOAK to MDW
Sort By:DepartureDurationArrivalPrice
Delta Air Lines
Delta Air Lines
DL-3903
17:55
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
13H :19 M
2 Stops
SLC · 3h 00mSalt Lake City (SLC), United States
DTW · 3h 31mDetroit (DTW), United States
09:14
2026-06-07
Chicago (MDW)United StatesMidway
$387
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
10H :33 M
2 Stops
SLC · 2h 15mSalt Lake City (SLC), United States
DTW · 1h 42mDetroit (DTW), United States
18:33
2026-06-06
Chicago (MDW)United StatesMidway
$469
total fare
Non Refundable 4 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
19H :41 M
2 Stops
SLC · 2h 32mSalt Lake City (SLC), United States
ATL · 9h 26mAtlanta (ATL), United States
10:09
2026-06-07
Chicago (MDW)United StatesMidway
$575
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
31H :49 M
2 Stops
SLC · 2h 32mSalt Lake City (SLC), United States
ATL · 21h 32mAtlanta (ATL), United States
22:17
2026-06-07
Chicago (MDW)United StatesMidway
$575
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
18H :46 M
2 Stops
SLC · 3h 12mSalt Lake City (SLC), United States
DTW · 8h 43mDetroit (DTW), United States
09:14
2026-06-07
Chicago (MDW)United StatesMidway
$580
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
22H :18 M
2 Stops
SLC · 3h 12mSalt Lake City (SLC), United States
DTW · 12h 18mDetroit (DTW), United States
12:46
2026-06-07
Chicago (MDW)United StatesMidway
$580
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
28H :03 M
2 Stops
SLC · 3h 12mSalt Lake City (SLC), United States
DTW · 18h 00mDetroit (DTW), United States
18:31
2026-06-07
Chicago (MDW)United StatesMidway
$580
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-3903
17:55
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
16H :51 M
2 Stops
SLC · 3h 00mSalt Lake City (SLC), United States
DTW · 7h 06mDetroit (DTW), United States
12:46
2026-06-07
Chicago (MDW)United StatesMidway
$580
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-3903
17:55
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
22H :36 M
2 Stops
SLC · 3h 00mSalt Lake City (SLC), United States
DTW · 12h 48mDetroit (DTW), United States
18:31
2026-06-07
Chicago (MDW)United StatesMidway
$580
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
9H :56 M
2 Stops
SLC · 2h 21mSalt Lake City (SLC), United States
MSP · 1h 35mMinneapolis (MSP), United States
17:56
2026-06-06
Chicago (MDW)United StatesMidway
$590
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-3903
17:55
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
14H :14 M
2 Stops
SLC · 2h 45mSalt Lake City (SLC), United States
ATL · 3h 53mAtlanta (ATL), United States
10:09
2026-06-07
Chicago (MDW)United StatesMidway
$590
total fare
Non Refundable 7 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
18H :09 M
2 Stops
SLC · 2h 01mSalt Lake City (SLC), United States
MSP · 9h 55mMinneapolis (MSP), United States
08:37
2026-06-07
Chicago (MDW)United StatesMidway
$608
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
25H :14 M
2 Stops
SLC · 14h 55mSalt Lake City (SLC), United States
DTW · 3h 31mDetroit (DTW), United States
09:14
2026-06-07
Chicago (MDW)United StatesMidway
$669
total fare
Non Refundable 4 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
21H :37 M
2 Stops
SLC · 2h 32mSalt Lake City (SLC), United States
ATL · 11h 22mAtlanta (ATL), United States
12:05
2026-06-07
Chicago (MDW)United StatesMidway
$694
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4134
12:28
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
25H :48 M
2 Stops
SLC · 2h 32mSalt Lake City (SLC), United States
ATL · 15h 32mAtlanta (ATL), United States
16:16
2026-06-07
Chicago (MDW)United StatesMidway
$694
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
28H :46 M
2 Stops
SLC · 21h 05mSalt Lake City (SLC), United States
DTW · 1h 02mDetroit (DTW), United States
12:46
2026-06-07
Chicago (MDW)United StatesMidway
$696
total fare
Non Refundable 4 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
13H :09 M
2 Stops
SLC · 4h 42mSalt Lake City (SLC), United States
ATL · 0h 49mAtlanta (ATL), United States
21:09
2026-06-06
Chicago (MDW)United StatesMidway
$895
total fare
Non Refundable 4 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
26H :09 M
2 Stops
SLC · 2h 18mSalt Lake City (SLC), United States
ATL · 10h 07mAtlanta (ATL), United States
10:09
2026-06-07
Chicago (MDW)United StatesMidway
$1,968
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
28H :05 M
2 Stops
SLC · 2h 18mSalt Lake City (SLC), United States
ATL · 12h 03mAtlanta (ATL), United States
12:05
2026-06-07
Chicago (MDW)United StatesMidway
$1,968
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
32H :16 M
2 Stops
SLC · 2h 18mSalt Lake City (SLC), United States
ATL · 16h 13mAtlanta (ATL), United States
16:16
2026-06-07
Chicago (MDW)United StatesMidway
$1,968
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included
Delta Air Lines
Delta Air Lines
DL-4061
06:00
2026-06-06
Oakland (OAK)United StatesMetropolitan Oak Intl
38H :17 M
2 Stops
SLC · 2h 18mSalt Lake City (SLC), United States
ATL · 22h 13mAtlanta (ATL), United States
22:17
2026-06-07
Chicago (MDW)United StatesMidway
$1,968
total fare
Non Refundable 9 Seat Left Economy
Cabin: Included

Recommended hotels in Chicago

Stay options near the arrival city for the same travel date.

Search hotels
WoodSpring Suites Chicago Addison
3.0Very GoodLive availability

WoodSpring Suites Chicago Addison

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Admiral Motel By OYO Chicago I-94
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Admiral Motel By OYO Chicago I-94

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Free WiFiACBreakfast
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$102per night+ taxes if applicable

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Woodspring Suites Downers Grove - Chicago
3.0Very GoodLive availability

Woodspring Suites Downers Grove - Chicago

- 2751 Ogden Ave 60515 Chicago Illinois United States Of America,

Free WiFiACBreakfast
Room availability is checked live
$106per night+ taxes if applicable

1 Night • 3 Star

Wyndham Garden Schaumburg Chicago Northwest
3.0Very GoodLive availability

Wyndham Garden Schaumburg Chicago Northwest

- 1725 E Algonquin Rd, Schaumburg, IL 60173 ,

Free WiFiACBreakfast
Room availability is checked live
$116per night+ taxes if applicable

1 Night • 3 Star

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Fare highlights

Selected flight highlights for 06 Jun 2026.

Open full search
Lowest fare $387 Delta Air Lines 17:55
Earliest departure $469 Delta Air Lines 06:00
Shortest duration $590 Delta Air Lines 06:00
Night 00:00-05:59 No option Open full search for more
Morning 06:00-11:59 $469 Delta Air Lines at 06:00
Afternoon 12:00-17:59 $387 Delta Air Lines at 17:55
Evening 18:00-23:59 No option Open full search for more

Oakland to Chicago route details

Oakland (OAK)

Metropolitan Oak Intl

United States

GMT -8

Latitude: 37.721298

Longitude: -122.221001

Chicago (MDW)

Midway

United States

GMT -6

Latitude: 41.785999

Longitude: -87.752403

Distance: Oakland (OAK), United States to Chicago (MDW), United States - 2,960.86 km
Flights shown for 06 Jun 2026. View all flights opens the complete search result.

Oakland to Chicago - what to expect when booking

The OAK to MDW cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.

Approx route distance: 2,960.86 km.

Before you book

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More flights from Oakland (OAK)24 routes
Oakland → Albuquerque
OAK → ABQ
Oakland → Austin
OAK → AUS
Oakland → Bellingham
OAK → BLI
Oakland → Boise
OAK → BOI
Oakland → Burbank
OAK → BUR
Oakland → Columbus
OAK → CMH
Oakland → Denver
OAK → DEN
Oakland → Eugene
OAK → EUG
Oakland → Dallas
OAK → DFW
Oakland → Guadalajara
OAK → GDL
Oakland → Honolulu
OAK → HNL
Oakland → Houston
OAK → HOU
Oakland → Kahului
OAK → OGG
Oakland → Kansas City
OAK → MCI
Oakland → Kona
OAK → KOA
Oakland → Las Vegas
OAK → LAS
Oakland → Kauai Island
OAK → LIH
Oakland → Long Beach
OAK → LGB
Oakland → Los Angeles
OAK → LAX
Oakland → Minneapolis
OAK → MSP
Oakland → New York
OAK → JFK
Oakland → Oklahoma City
OAK → OKC
Oakland → Ontario
OAK → ONT
Oakland → Phoenix
OAK → PHX
More flights from Chicago (MDW)24 routes
Chicago → Albany
MDW → ALB
Chicago → Albuquerque
MDW → ABQ
Chicago → Amarillo
MDW → AMA
Chicago → Atlanta
MDW → ATL
Chicago → Austin
MDW → AUS
Chicago → Birmingham
MDW → BHM
Chicago → Boston
MDW → BOS
Chicago → Buffalo Ny
MDW → BUF
Chicago → Cancun
MDW → CUN
Chicago → Charleston
MDW → CHS
Chicago → Charlotte
MDW → CLT
Chicago → Cleveland
MDW → CLE
Chicago → Columbus
MDW → CMH
Chicago → Denver
MDW → DEN
Chicago → Des Moines
MDW → DSM
Chicago → Detroit Mi
MDW → DTW
Chicago → Fort Lauderdale
MDW → FLL
Chicago → Fort Myers
MDW → RSW
Chicago → Greenville
MDW → GSP
Chicago → Guadalajara
MDW → GDL
Chicago → Windsor Locks
MDW → BDL
Chicago → Houston
MDW → HOU
Chicago → Jackson
MDW → JAN
Chicago → Jacksonville
MDW → JAX
Frequently asked questions - Oakland to Chicago flights
Generally yes. When your travel date is fixed, comparing live fares early gives you better visibility of timings, baggage and fare rules before prices change.
The approximate route distance between Oakland (OAK) and Chicago (MDW) is 2,960.86 km. Actual flying distance can vary by airline routing.
Availability changes by airline schedule and date. Use the Stops filter to quickly check non-stop, one-stop and connecting options on this landing page.
Airline inventory can change within minutes. Book Now sends the selected result to the review flow where the fare is checked again before final booking.
Yes. The date strip and search box open the full search for the selected date, while this page keeps the route details easy to compare.