Compare 8 loyalty programs for San Diego to Chicago award flights, with economy seats from 90 points.
San Diego to Chicago is a medium-haul domestic corridor with nonstop award seats on United Airlines and Alaska Airlines. Award pricing spans eight programs, and economy starts at 90 points on a United Airlines nonstop. Lufthansa Miles & More prices that seat lowest, so defaulting to United Airlines' own program can mean overpaying. Every SAN–ORD award below is re-priced daily, program by program.
Best one-way award prices per airline over the next 12 months.
| Airline | Economy | Business | First |
|---|---|---|---|
 United AirlinesUA | 90Lowest | Not available | 46,300pts |
 American AirlinesAA | 8,500pts | 40,000Lowest | 18,000Lowest |
 Alaska AirlinesAS | 10,000pts | 46,000pts | 25,000pts |
 DeltaDL | 11,200pts | Not available | 51,300pts |
 JetBlueB6 | 15,900pts | 81,000pts | Not available |
When award seats between San Diego and Chicago price cheapest over the next year.
| Month | Cheapest award (points) |
|---|---|
| Nov 2026 | 90 |
| Dec 2026 | 8,974 |
| Jan 2027 | No award data |
| Feb 2027 | No award data |
| Mar 2027 | 8,500 |
| Apr 2027 | No award data |
| May 2027 | No award data |
| Jun 2027 | No award data |
| Jul 2027 | No award data |
| Aug 2027 | 8,500 |
| Sep 2027 | No award data |
| Oct 2027 | No award data |
5 airlines with award seats between San Diego and Chicago, nonstop or connecting.
American AirlinesAAAlaska AirlinesASJetBlueB6DeltaDLUnited AirlinesUAWhat to know before booking San Diego to Chicago with points.
About 1,720 miles, roughly 3h55 nonstop. Local time in Chicago is 2 hours ahead of San Diego. Award data window: November 2026–November 2027, with calendar prices for four months. Across well-covered months, November 2026 is the cheapest (90 points), ahead of March and August 2027 (8,500).
San Diego to Chicago is served by American Airlines, Alaska Airlines, JetBlue and 2 more, offering multiple options for award travelers. Compare 8 loyalty programs to find the best value for your points. Award prices start from 90 points in economy. Use our search tool to check real-time award availability on this route.
Roughly 1,720 miles separate San Diego International Airport (SAN) and Chicago's O'Hare International Airport (ORD), so a nonstop spends about 3h55 in the air, a little more or less depending on winds and direction. United Airlines and Alaska Airlines both carry nonstop award space in the data. Aircraft logged on those nonstops include the Airbus A321neo and Boeing 737-900. About 15% of the award options in the data are nonstop.
San Diego–Chicago is domestic, so price it in cash before you price it in points. The economy floor is a partner booking on a United Airlines nonstop, with no connection to trade off against the points. That seat adds about $319 in taxes and fees, well above the route's typical economy taxes, so weigh points and cash together before booking. When the fare is low, pay cash and hold the points for a pricier trip.
Lufthansa Miles & More wins economy at 90 points on a United Airlines nonstop. Etihad Guest takes business class at 40,000 points. American AAdvantage is cheapest in first class at 18,000 points. Of the other five, JetBlue TrueBlue, Delta SkyMiles, and Alaska Atmos Rewards are worth a look too. Business class is also priced as a partner award, so the miles and the metal come from different airlines.
Two airlines show nonstop award space on San Diego–Chicago: United Airlines (Star Alliance) and Alaska Airlines (oneworld). Partner programs in both alliances can price a nonstop here, not just the carriers' own. Partner pricing sets the economy floor: Lufthansa Miles & More books United Airlines as a Star Alliance partner, and no program prices United Airlines lower in that cabin at last check. With only five airlines holding award seats but eight programs pricing them, the currency you book with matters more than the carrier.
San Diego and Chicago each show a single airport in the data for this route, so the calendar is where the savings are. Pricing the round trip? Chicago to San Diego is tracked separately, and awards can price differently each way.
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Common questions travelers ask about the San Diego to Chicago route.
