San Antonio to Chicago: what the flight costs
In the last 60 days we checked this route 13 times. The typical return was £346 per person and the lowest £324, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £324 |
| Typical (median) | £346 |
| Price checks, 60 days | 13 |
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Trips we picked on this route
Just found · from San AntonioLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Fare is $430 per person, $29 below the typical fare on this route
- Breakfast and free cancellation at La Quinta, reviewed 8 by 3,744 guests
- Dry, overcast Saturday and Sunday, highs 58°F and 65°F, 1% rain
£1,283 for two · 2 nights · flights, hotel, taxes & fees
Flights £648 + hotel £635, taxes in · a checked bag each adds about £181
Frontier · with a stop · 8h 59m
The catch: The Frontier outbound has one stop and takes 8h 59m, and a checked bag is about $240 for two, which isn't in the total.
Worth it if you pack light and want a walkable Loop weekend of museums and food; skip it if 8h 59m with a stop would eat your Friday.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 14 Oct 2026 | 16 – 18 Oct 2026 | £412 | F9 | with a stop | 21h 55m | Kiwi.com |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £344 | F9 | with a stop | 8h 59m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £410 | F9 | with a stop | 8h 59m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £453 | Y4 + VB | with a stop | 27h | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £324 | Frontier | with a stop | 8h 59m | Google Flights |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £345 | F9 | with a stop | 8h 59m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £346 | F9 | with a stop | 28h 3m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £387 | Y4 + VB | with a stop | 27h | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £324 | Frontier | with a stop | 28h 3m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £417 | VB + Y4 | with a stop | 24h 58m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £324 | Frontier | with a stop | 8h 59m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £350 | F9 | with a stop | 28h 3m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £345 | F9 | with a stop | 8h 59m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about San Antonio to Chicago
What does a return from San Antonio to Chicago usually cost?
Over the last 60 days the typical price we found was £346 per person, taxes and fees included, across 13 checks; the lowest was £324.
When is the best time to fly from San Antonio to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from San Antonio to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.