San Antonio (SAT) to Chicago (ORD) · Dec 29, 2026 · return Jan 1, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 29 – Jan 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $374 total · 4★ The Royal Sonesta Chicago River North, $484 total · 5★ Nobu Hotel Chicago, $1,340 total

All hotels in Chicago

Route overview: San Antonio to Chicago (ORD) flight deals

2026-12-29 → 2027-01-01 · Axel-exclusive $430.66

• American Airlines AA961: SAT 2026-12-29 07:34:00 → ORD 2026-12-29 10:35:00; nonstop; 181 minutes. Local airport times.
• American Airlines AA857: ORD 2027-01-01 20:53:00 → SAT 2027-01-01 23:55:00; nonstop; 182 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $444.16

• United Airlines UA5805: SAT 2026-12-29 17:39:00 → ORD 2026-12-29 20:40:00; nonstop; 181 minutes. Local airport times.
• United Airlines UA1394: ORD 2027-01-01 19:45:00 → SAT 2027-01-01 22:59:00; nonstop; 194 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $376.66

• Frontier Airlines F92355 / F93174: SAT 2026-12-29 18:47:00 → ORD 2026-12-30 00:54:00; 1 stop(s) via DEN; 367 minutes. Local airport times.
  • F92355: SAT 2026-12-29 18:47:00 → DEN 2026-12-29 20:09:00; layover at DEN: 77 minutes.
  • F93174: DEN 2026-12-29 21:26:00 → ORD 2026-12-30 00:54:00.
• United Airlines UA1394: ORD 2027-01-01 19:45:00 → SAT 2027-01-01 22:59:00; nonstop; 194 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $457.66

• Delta Air Lines DL2717 / DL1567: SAT 2026-12-29 06:00:00 → ORD 2026-12-29 11:44:00; 1 stop(s) via MSP; 344 minutes. Local airport times.
  • DL2717: SAT 2026-12-29 06:00:00 → MSP 2026-12-29 08:52:00; layover at MSP: 68 minutes.
  • DL1567: MSP 2026-12-29 10:00:00 → ORD 2026-12-29 11:44:00.
• Delta Air Lines DL2738 / DL1508: ORD 2027-01-01 18:40:00 → SAT 2027-01-02 00:40:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • DL2738: ORD 2027-01-01 18:40:00 → ATL 2027-01-01 21:58:00; layover at ATL: 61 minutes.
  • DL1508: ATL 2027-01-01 22:59:00 → SAT 2027-01-02 00:40:00.

2026-12-29 → 2027-01-01 · Axel-exclusive $525.16

• VB VB675 / VB632: SAT 2026-12-29 17:10:00 → ORD 2026-12-29 23:00:00; 1 stop(s) via MTY; 350 minutes. Local airport times.
  • VB675: SAT 2026-12-29 17:10:00 → MTY 2026-12-29 18:20:00; layover at MTY: 75 minutes.
  • VB632: MTY 2026-12-29 19:35:00 → ORD 2026-12-29 23:00:00.
• United Airlines UA1394: ORD 2027-01-01 19:45:00 → SAT 2027-01-01 22:59:00; nonstop; 194 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $430.66

• American Airlines AA4551: SAT 2026-12-29 18:36:00 → ORD 2026-12-29 21:46:00; nonstop; 190 minutes. Local airport times.
• American Airlines AA857: ORD 2027-01-01 20:53:00 → SAT 2027-01-01 23:55:00; nonstop; 182 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $444.16

• United Airlines UA1332: SAT 2026-12-29 06:35:00 → ORD 2026-12-29 09:32:00; nonstop; 177 minutes. Local airport times.
• United Airlines UA1394: ORD 2027-01-01 19:45:00 → SAT 2027-01-01 22:59:00; nonstop; 194 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $417.16

• American Airlines AA2070 / AA2065: SAT 2026-12-29 08:00:00 → ORD 2026-12-29 14:12:00; 1 stop(s) via DFW; 372 minutes. Local airport times.
  • AA2070: SAT 2026-12-29 08:00:00 → DFW 2026-12-29 09:22:00; layover at DFW: 142 minutes.
  • AA2065: DFW 2026-12-29 11:44:00 → ORD 2026-12-29 14:12:00.
• American Airlines AA857: ORD 2027-01-01 20:53:00 → SAT 2027-01-01 23:55:00; nonstop; 182 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $430.66

• United Airlines UA6246 / UA2296: SAT 2026-12-29 14:19:00 → ORD 2026-12-29 20:00:00; 1 stop(s) via IAH; 341 minutes. Local airport times.
  • UA6246: SAT 2026-12-29 14:19:00 → IAH 2026-12-29 15:28:00; layover at IAH: 99 minutes.
  • UA2296: IAH 2026-12-29 17:07:00 → ORD 2026-12-29 20:00:00.
• United Airlines UA1394: ORD 2027-01-01 19:45:00 → SAT 2027-01-01 22:59:00; nonstop; 194 minutes. Local airport times.

2026-12-29 → 2027-01-01 · Axel-exclusive $457.66

• Delta Air Lines DL1408 / DL2879: SAT 2026-12-29 13:00:00 → ORD 2026-12-29 19:05:00; 1 stop(s) via ATL; 365 minutes. Local airport times.
  • DL1408: SAT 2026-12-29 13:00:00 → ATL 2026-12-29 16:19:00; layover at ATL: 86 minutes.
  • DL2879: ATL 2026-12-29 17:45:00 → ORD 2026-12-29 19:05:00.
• Delta Air Lines DL2738 / DL1508: ORD 2027-01-01 18:40:00 → SAT 2027-01-02 00:40:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • DL2738: ORD 2027-01-01 18:40:00 → ATL 2027-01-01 21:58:00; layover at ATL: 61 minutes.
  • DL1508: ATL 2027-01-01 22:59:00 → SAT 2027-01-02 00:40:00.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Antonio (SAT) to Chicago (ORD) · Dec 29, 2026 · return Jan 1, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• 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.
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• 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.

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