# San Diego (SAN) to Chicago (ORD), Dec 16, 2026: round trips from $200, one way from $105 San Diego (SAN) to Chicago (ORD), Dec 16, 2026: round trips from $200, one way from $105 on Axel, checked Nov 11, 2026. Lowest published fares: $200 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Dec 16–17, 2026; $105 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 16, 2026; 1 adult, economy, checked Nov 11, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply. **Prices by return date:** match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown. **Date links** open published trip details for exploration. **Price links** open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked | | --- | --- | --- | --- | ---: | --- | | [2026-12-16 · one way](https://helloaxel.com/en/flights/choose/san-ord/dec-16/one-way) | Alaska Airlines | AS1478 | 12:42:00→19:00:00 4h 18m nonstop | [Axel-exclusive $180.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/trip/one-way/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 · one way](https://helloaxel.com/en/flights/choose/san-ord/dec-16/one-way) | Frontier Airlines | F92422 + F93174 | 16:16:00→00:26:00 6h 10m 1 stop via DEN | [Axel-exclusive $105.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/trip/one-way/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-17](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-17) | Alaska Airlines | AS1478 / AS1479 | 12:42:00→19:00:00 4h 18m nonstop · 19:58:00→22:49:00 4h 51m nonstop | [Axel-exclusive $345.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-17-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-17](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-17) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $200.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-17-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-18](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-18) | Alaska Airlines | AS1478 / AS1479 | 12:42:00→19:00:00 4h 18m nonstop · 19:58:00→22:49:00 4h 51m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-18-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-18](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-18) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-18-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-19](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-19) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:17:00→17:02:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-19-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-19](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-19) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-19-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-20](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-20) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:17:00→17:02:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-20-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-20](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-20) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-20-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-21](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-21) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:13:00→17:00:00 4h 47m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-21-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-21](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-21) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-21-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-22](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-22) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:13:00→17:00:00 4h 47m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-22-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-22](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-22) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-22-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-23](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-23) | Alaska Airlines | AS1478 / AS1470 | 12:42:00→19:00:00 4h 18m nonstop · 07:27:00→10:12:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-23-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-23](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-23) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-23-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-24](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-24) | Alaska Airlines | AS1478 / AS1479 | 12:42:00→19:00:00 4h 18m nonstop · 19:58:00→22:49:00 4h 51m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-24-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-24](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-24) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-24-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-25](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-25) | Alaska Airlines | AS1478 / AS1479 | 12:42:00→19:00:00 4h 18m nonstop · 19:58:00→22:49:00 4h 51m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-25-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-25](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-25) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-25-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-26](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-26) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:17:00→17:02:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-26-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-26](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-26) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-26-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-27](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-27) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:17:00→17:02:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-27-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-27](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-27) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-27-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-28](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-28) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:13:00→17:00:00 4h 47m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-28-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-28](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-28) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-28-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-29](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-29) | Alaska Airlines | AS1478 / AS1447 | 12:42:00→19:00:00 4h 18m nonstop · 14:13:00→17:00:00 4h 47m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-29-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-29](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-29) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-29-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-30](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-30) | Alaska Airlines | AS1478 / AS1470 | 12:42:00→19:00:00 4h 18m nonstop · 07:27:00→10:12:00 4h 45m nonstop | [Axel-exclusive $414.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-30-2026/adults/1/cabin/economy) | Nov 11, 2026 | | [2026-12-16 → 2026-12-30](https://helloaxel.com/en/flights/choose/san-ord/dec-16/dec-30) | Frontier Airlines | F92422 + F93174 / F92145 + F91326 | 16:16:00→00:26:00 6h 10m 1 stop via DEN · 06:21:00→11:37:00 7h 16m 1 stop via LAS | [Axel-exclusive $240.00](https://helloaxel.com/en/f/start/from/san/to/ord/depart/december-16-2026/return/december-30-2026/adults/1/cabin/economy) | Nov 11, 2026 | ### Hotels in Chicago for these trips **Hotels:** under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates. - Hotels in Chicago for these nights (Dec 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ [Hotel Versey, $80 a night](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-17/2-adults) · 4★ [Warwick Allerton - Chicago, $89 a night](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-17/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $203 a night](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-17/2-adults) - Hotels in Chicago for these nights (Dec 16–18, 2026 · 2 nights · 2 adults, 1 room): 3★ [Hotel Versey, $83 a night, $166 for 2 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-18/2-adults) · 4★ [Warwick Allerton - Chicago, $92 a night, $183 for 2 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-18/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $205 a night, $410 for 2 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-18/2-adults) - Hotels in Chicago for these nights (Dec 16–19, 2026 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $94 a night, $283 for 3 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-19/2-adults) · 4★ [Warwick Allerton - Chicago, $103 a night, $308 for 3 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-19/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $205 a night, $616 for 3 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-19/2-adults) - Hotels in Chicago for these nights (Dec 16–20, 2026 · 4 nights · 2 adults, 1 room): 3★ [Hotel Versey, $101 a night, $402 for 4 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-20/2-adults) · 4★ [Warwick Allerton - Chicago, $107 a night, $428 for 4 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-20/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $234 a night, $937 for 4 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-20/2-adults) - Hotels in Chicago for these nights (Dec 16–21, 2026 · 5 nights · 2 adults, 1 room): 3★ [Hotel Versey, $96 a night, $478 for 5 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-21/2-adults) · 4★ [Warwick Allerton - Chicago, $103 a night, $517 for 5 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-21/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $229 a night, $1,143 for 5 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-21/2-adults) - Hotels in Chicago for these nights (Dec 16–22, 2026 · 6 nights · 2 adults, 1 room): 3★ [Hotel Versey, $93 a night, $558 for 6 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-22/2-adults) · 4★ [Warwick Allerton - Chicago, $101 a night, $606 for 6 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-22/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $225 a night, $1,347 for 6 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-22/2-adults) - Hotels in Chicago for these nights (Dec 16–23, 2026 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $91 a night, $639 for 7 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-23/2-adults) · 4★ [Warwick Allerton - Chicago, $99 a night, $695 for 7 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-23/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $222 a night, $1,553 for 7 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-23/2-adults) - Hotels in Chicago for these nights (Dec 16–24, 2026 · 8 nights · 2 adults, 1 room): 3★ [Hotel Versey, $92 a night, $738 for 8 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-24/2-adults) · 4★ [Warwick Allerton - Chicago, $99 a night, $791 for 8 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-24/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $220 a night, $1,760 for 8 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-24/2-adults) - Hotels in Chicago for these nights (Dec 16–25, 2026 · 9 nights · 2 adults, 1 room): 3★ [Hotel Versey, $95 a night, $855 for 9 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-25/2-adults) · 4★ [Warwick Allerton - Chicago, $99 a night, $887 for 9 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-25/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $218 a night, $1,959 for 9 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-25/2-adults) - Hotels in Chicago for these nights (Dec 16–26, 2026 · 10 nights · 2 adults, 1 room): 3★ [Hotel Versey, $99 a night, $989 for 10 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-26/2-adults) · 4★ [Warwick Allerton - Chicago, $101 a night, $1,005 for 10 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-26/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $217 a night, $2,169 for 10 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-26/2-adults) - Hotels in Chicago for these nights (Dec 16–27, 2026 · 11 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $101 a night, $1,114 for 11 nights](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-12-16/2026-12-27/2-adults) · 4★ [Warwick Allerton - Chicago, $102 a night, $1,119 for 11 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-27/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $216 a night, $2,375 for 11 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-27/2-adults) - Hotels in Chicago for these nights (Dec 16–28, 2026 · 12 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $101 a night, $1,208 for 12 nights](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-12-16/2026-12-28/2-adults) · 4★ [Warwick Allerton - Chicago, $101 a night, $1,215 for 12 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-28/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $215 a night, $2,585 for 12 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-28/2-adults) - Hotels in Chicago for these nights (Dec 16–29, 2026 · 13 nights · 2 adults, 1 room): 3★ [Hotel Versey, $100 a night, $1,295 for 13 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-29/2-adults) · 4★ [Warwick Allerton - Chicago, $101 a night, $1,311 for 13 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-29/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $215 a night, $2,791 for 13 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-29/2-adults) - Hotels in Chicago for these nights (Dec 16–30, 2026 · 14 nights · 2 adults, 1 room): 3★ [Hotel Versey, $99 a night, $1,380 for 14 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-16/2026-12-30/2-adults) · 4★ [Warwick Allerton - Chicago, $100 a night, $1,405 for 14 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-16/2026-12-30/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $214 a night, $2,998 for 14 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-16/2026-12-30/2-adults) [All hotels in Chicago](https://helloaxel.com/en/hotels/destinations/chicago) [Route overview: San Diego to Chicago (ORD) flight deals](/en/flights/from-san-diego-to-chicago-ord) ### 2026-12-16 · one way · Axel-exclusive $105.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. ### 2026-12-16 · one way · Axel-exclusive $180.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. ### 2026-12-16 → 2026-12-17 · Axel-exclusive $200.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-17 06:21:00 → SAN 2026-12-17 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-17 06:21:00 → LAS 2026-12-17 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-17 10:15:00 → SAN 2026-12-17 11:37:00. ### 2026-12-16 → 2026-12-17 · Axel-exclusive $345.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1479: ORD 2026-12-17 19:58:00 → SAN 2026-12-17 22:49:00; nonstop; 291 minutes. Local airport times. ### 2026-12-16 → 2026-12-18 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-18 06:21:00 → SAN 2026-12-18 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-18 06:21:00 → LAS 2026-12-18 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-18 10:15:00 → SAN 2026-12-18 11:37:00. ### 2026-12-16 → 2026-12-18 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1479: ORD 2026-12-18 19:58:00 → SAN 2026-12-18 22:49:00; nonstop; 291 minutes. Local airport times. ### 2026-12-16 → 2026-12-19 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-19 06:21:00 → SAN 2026-12-19 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-19 06:21:00 → LAS 2026-12-19 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-19 10:15:00 → SAN 2026-12-19 11:37:00. ### 2026-12-16 → 2026-12-19 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-19 14:17:00 → SAN 2026-12-19 17:02:00; nonstop; 285 minutes. Local airport times. ### 2026-12-16 → 2026-12-20 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-20 06:21:00 → SAN 2026-12-20 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-20 06:21:00 → LAS 2026-12-20 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-20 10:15:00 → SAN 2026-12-20 11:37:00. ### 2026-12-16 → 2026-12-20 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times. ### 2026-12-16 → 2026-12-22 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-22 06:21:00 → SAN 2026-12-22 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-22 06:21:00 → LAS 2026-12-22 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-22 10:15:00 → SAN 2026-12-22 11:37:00. ### 2026-12-16 → 2026-12-22 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-22 14:13:00 → SAN 2026-12-22 17:00:00; nonstop; 287 minutes. Local airport times. ### 2026-12-16 → 2026-12-23 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-23 06:21:00 → SAN 2026-12-23 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-23 06:21:00 → LAS 2026-12-23 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-23 10:15:00 → SAN 2026-12-23 11:37:00. ### 2026-12-16 → 2026-12-23 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1470: ORD 2026-12-23 07:27:00 → SAN 2026-12-23 10:12:00; nonstop; 285 minutes. Local airport times. ### 2026-12-16 → 2026-12-24 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-24 06:21:00 → SAN 2026-12-24 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-24 06:21:00 → LAS 2026-12-24 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-24 10:15:00 → SAN 2026-12-24 11:37:00. ### 2026-12-16 → 2026-12-24 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1479: ORD 2026-12-24 19:58:00 → SAN 2026-12-24 22:49:00; nonstop; 291 minutes. Local airport times. ### 2026-12-16 → 2026-12-26 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-26 06:21:00 → SAN 2026-12-26 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-26 06:21:00 → LAS 2026-12-26 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-26 10:15:00 → SAN 2026-12-26 11:37:00. ### 2026-12-16 → 2026-12-26 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-26 14:17:00 → SAN 2026-12-26 17:02:00; nonstop; 285 minutes. Local airport times. ### 2026-12-16 → 2026-12-27 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-27 06:21:00 → SAN 2026-12-27 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-27 06:21:00 → LAS 2026-12-27 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-27 10:15:00 → SAN 2026-12-27 11:37:00. ### 2026-12-16 → 2026-12-27 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-27 14:17:00 → SAN 2026-12-27 17:02:00; nonstop; 285 minutes. Local airport times. ### 2026-12-16 → 2026-12-28 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-28 06:21:00 → SAN 2026-12-28 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-28 06:21:00 → LAS 2026-12-28 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-28 10:15:00 → SAN 2026-12-28 11:37:00. ### 2026-12-16 → 2026-12-28 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times. ### 2026-12-16 → 2026-12-30 · Axel-exclusive $240.00 - Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times. - F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes. - F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00. - Frontier Airlines F92145 / F91326: ORD 2026-12-30 06:21:00 → SAN 2026-12-30 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times. - F92145: ORD 2026-12-30 06:21:00 → LAS 2026-12-30 08:34:00; layover at LAS: 101 minutes. - F91326: LAS 2026-12-30 10:15:00 → SAN 2026-12-30 11:37:00. ### 2026-12-16 → 2026-12-30 · Axel-exclusive $414.00 - Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times. - Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/san-ord) - [Dec 15, 2026 · Return options](/en/flights/choose/san-ord/dec-15) - [Dec 17, 2026 · Return options](/en/flights/choose/san-ord/dec-17) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** San Diego (SAN) to Chicago (ORD) · Dec 16, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates. - **Next:** each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: [Choose travelers and dates](https://helloaxel.com/en/f/start/from/san/to/ord/step/travelers) prices the requested trip. - **Follow supplied links.** For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links. - **If links fail or are missing:** If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: [Axel San Diego to Chicago (ORD) flight deals](https://helloaxel.com/en/flights/from-san-diego-to-chicago-ord) · [Flight search guide](https://helloaxel.com/en/ai). - **Sharing with the traveler:** Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct `https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback` using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace `/return/YYYY-MM-DD` with `/trip/oneway`. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. [Preferences and advanced options](https://helloaxel.com/en/ai#customer-fallback-link). **Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/san-ord/dec-16?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/san-ord/dec-16?axel_reason=product_issue&axel_scope=product)