San Jose to Chicago SJC → MDW, ORD
Norman Y. Mineta San Jose International Airport (SJC) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $376 with Alaska Airlines, 11 Nov – 14 Nov, found yesterday. The cheapest one-way found recently is $195 with Alaska Airlines, 31 Mar 2027, found yesterday.
Return
The cheapest return fare on each of 5 departure dates is usually $415 to $524.
Cheapest return found recently
$376
11 Nov – 14 Nov · Alaska Airlines
Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD)
Leaves 9:39 a.m. · Return leaves 7:20 a.m. · 14 h 37 min of travel, both ways together
out 1 stop, back 1 stop
found yesterday
Cheapest nonstop return
$419
14 Nov – 17 Nov · United Airlines
Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD)
Leaves 2:14 p.m. · Return leaves 9:55 a.m. · 9 h 8 min of travel, both ways together
out nonstop, back nonstop
found 4 days ago
Found recently, and the cheapest we hold
$376 11 Nov – 14 Novfound yesterdaySee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $288 to $479.
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?
No. We hold 3-night return fares on 1 other departure date within 3 days of 11 Nov, and it is not cheaper.
Every date we hold
6 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 4 Nov – 3 Dec | $415 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found today | See prices for these dates |
| 5 Nov – 30 Nov | $524 | Southwest Airlines | Norman Y. Mineta San Jose International Airport (SJC) → Chicago Midway International Airport (MDW) | out nonstop, back 1 stop | found today | See prices for these dates |
| 11 Nov – 14 Nov | $376 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| 14 Nov – 17 Nov | $419 | United Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 24 Nov – 28 Nov | $654 | American Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
Airlines on the cheapest dates: Alaska Airlines, Southwest Airlines, United Airlines, American Airlines.
One-way
The cheapest one-way fare on each of 7 departure dates is usually $177 to $195.
Cheapest one-way found recently
$195
31 Mar 2027 · Alaska Airlines
Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD)
Leaves 7:05 a.m. · 9 h 50 min trip
1 stop
found yesterday
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$195 31 Mar 2027found yesterdayOpen this trip
$165 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 $156 to $189.
At $195, 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 7 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?
We hold no other one-way fares leaving within 3 days of 31 Mar 2027 to compare.
Every date we hold
7 fares on 7 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Nov | $195 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 5 Jan 2027 | $165 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 7 Jan 2027 | $165 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 31 Mar 2027 | $195 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 19 Apr 2027 | $192 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 19 Jul 2027 | $209 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
| 20 Jul 2027 | $188 | Alaska Airlines | Norman Y. Mineta San Jose International Airport (SJC) → 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 $165.
Airlines on the cheapest dates: Alaska Airlines.
Premium cabin fares from San Jose 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 31 Mar 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for San Jose to Chicago?
Return
Fares 90 to 179 days before departure were typically 49% 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 | $589 | $582 | +97% | 10 |
| 7–13 days | $474 | $336 | +59% | 14 |
| 14–29 days | $330 | $288 | +10% | 17 |
| 30–59 days | $503 | $330 | +68% | 19 |
| 60–89 days | $873 | $427 | +192% | 17 |
| 90–179 days | $299 | $299 | Cheapest seen | 8 |
| 180+ days | $342 | $342 | +14% | 11 |
One-way
The cheapest fares were 60 to 89 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 | $170 | $156 | +3% | 8 |
| 60–89 days | $165 | $165 | Cheapest seen | 11 |
| 90–179 days | $181 | $180 | +10% | 20 |
| 180+ days | $180 | $179 | +9% | 25 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
San Francisco → Chicago
67 km from San Jose
$301
$75 less than flying from San Jose
11 Nov – 14 Nov · SFO → ORD · out 1 stop, back 1 stop
found yesterday
Sacramento → Chicago
142 km from San Jose
$347
$29 less than flying from San Jose
14 Nov – 20 Nov · SMF → ORD · out 1 stop, back 1 stop
found today
Oakland → Chicago
61 km from San Jose
$381
$5 more than flying from San Jose
11 Nov – 14 Nov · OAK → ORD · out 1 stop, back 1 stop
found yesterday
San Jose → Milwaukee
131 km from Chicago
$677
$301 more than flying to Chicago
6 Nov – 7 Nov · SJC → 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 Francisco → Chicago
67 km from San Jose
$201
$6 more than flying from San Jose
31 Mar 2027 · SFO → ORD · 1 stop
found yesterday
Oakland → Chicago
61 km from San Jose
$210
$15 more than flying from San Jose
23 Nov · OAK → 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