Oakland to Chicago OAK → MDW, ORD
Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $381 with Alaska Airlines, 11 Nov – 14 Nov, found yesterday. The cheapest one-way found recently is $210 with Alaska Airlines, 23 Nov, found yesterday.
Return
The cheapest return fare on each of 5 departure dates is usually $381 to $521.
Cheapest return found recently
$381
11 Nov – 14 Nov · Alaska Airlines
Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD)
Leaves 7:52 p.m. · Return leaves 7:20 a.m. · 15 h 5 min of travel, both ways together
out 1 stop, back 1 stop
found yesterday
Cheapest nonstop return
$409
4 Nov – 3 Dec · Southwest Airlines
Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW)
Leaves 6:30 a.m. · Return leaves 9:05 p.m. · 8 h 50 min of travel, both ways together
out nonstop, back nonstop
found today
Found recently, and the cheapest we hold
$381 11 Nov – 14 Novfound yesterdaySee prices for these dates
$345 14 Nov – 17 Novfound 4 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $265 to $366.
At $381, the cheapest return found recently is above that range.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 5 departure dates from 4 Nov to 24 Nov, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
Yes. Among 3-night return fares leaving within 3 days of 11 Nov, 14 Nov – 17 Nov costs $345: $36 less than the cheapest found recently.
Alaska Airlines · Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) · out 1 stop, back 1 stop · found 4 days ago
Every date we hold
8 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 4 Nov – 3 Dec | $409 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found today | See prices for these dates |
| 5 Nov – 30 Nov | $521 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | out nonstop, back 1 stop | found today | See prices for these dates |
| 11 Nov – 14 Nov | $381 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| 14 Nov – 17 Nov | $345 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| 24 Nov – 28 Nov | $817 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
Airlines on the cheapest dates: Southwest Airlines, Alaska Airlines.
One-way
The cheapest one-way fare on each of 8 departure dates is usually $201 to $218.
Cheapest one-way found recently
$210
23 Nov · Alaska Airlines
Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD)
Leaves 9:53 a.m. · 8 h 10 min trip
1 stop
found yesterday
Cheapest nonstop one-way
$219
31 Mar 2027 · Southwest Airlines
Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW)
Leaves 11:45 p.m. · 4 h 5 min trip
nonstop
found yesterday
Found recently, and the cheapest we hold
$210 23 Novfound yesterdayOpen this trip
$194 5 Jan 2027found 5 days agoOpen this trip
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $130 to $194.
At $210, the cheapest one-way found recently is above that range.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 8 departure dates from 23 Nov to 20 Jul 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
No. We hold one-way fares on 1 other departure date within 3 days of 23 Nov, and it is not cheaper.
Every date we hold
10 fares on 8 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Nov | $210 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 25 Nov | $263 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | 1 stop | found 2 days ago | Open this trip |
| 5 Jan 2027 | $194 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 7 Jan 2027 | $199 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | nonstop | found 5 days ago | Open this trip |
| 31 Mar 2027 | $219 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | nonstop | found yesterday | Open this trip |
| 19 Apr 2027 | $218 | Southwest Airlines | Metropolitan Oakland International Airport (OAK) → Chicago Midway International Airport (MDW) | nonstop | found 5 days ago | Open this trip |
| 19 Jul 2027 | $210 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
| 20 Jul 2027 | $202 | Alaska Airlines | Metropolitan Oakland International Airport (OAK) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
Which month looks cheapest?
January 2027 is the cheapest month — from $194.
Airlines on the cheapest dates: Alaska Airlines, Southwest Airlines.
Premium cabin fares from Oakland to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 11 Nov – 14 Nov in another cabin: Premium economy · Business · First
Today's prices for 23 Nov in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Oakland to Chicago?
Return
Fares 90 to 179 days before departure were typically 30% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $490 | $467 | +42% | 11 |
| 7–13 days | $359 | $359 | +4% | 11 |
| 14–29 days | $345 | $265 | +0% | 17 |
| 30–59 days | $467 | $345 | +36% | 15 |
| 60–89 days | $366 | $366 | +6% | 15 |
| 90–179 days | $344 | $344 | Cheapest seen | 8 |
| 180+ days | $380 | $380 | +11% | 11 |
One-way
Fares 90 to 179 days before departure were typically 12% lower than 30 to 59 days before departure.
From the cheapest one-way each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 30–59 days | $209 | $130 | +14% | 8 |
| 60–89 days | $221 | $194 | +21% | 15 |
| 90–179 days | $183 | $181 | Cheapest seen | 20 |
| 180+ days | $196 | $192 | +7% | 25 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
San Francisco → Chicago
13 km from Oakland
$301
$80 less than flying from Oakland
11 Nov – 14 Nov · SFO → ORD · out 1 stop, back 1 stop
found yesterday
Sacramento → Chicago
110 km from Oakland
$347
$34 less than flying from Oakland
14 Nov – 20 Nov · SMF → ORD · out 1 stop, back 1 stop
found today
San Jose → Chicago
61 km from Oakland
$376
$5 less than flying from Oakland
11 Nov – 14 Nov · SJC → ORD · out 1 stop, back 1 stop
found yesterday
Oakland → Milwaukee
131 km from Chicago
$677
$296 more than flying to Chicago
6 Nov – 7 Nov · OAK → MKE · out 1 stop, back 1 stop
found 2 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
San Jose → Chicago
61 km from Oakland
$195
$15 less than flying from Oakland
31 Mar 2027 · SJC → ORD · 1 stop
found yesterday
San Francisco → Chicago
13 km from Oakland
$201
$9 less than flying from Oakland
31 Mar 2027 · SFO → ORD · 1 stop
found yesterday
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 11 Nov – 14 Nov. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work