Chicago from San Antonio, 16 – 18 Oct: £1,283 for two, all in
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The verdict
Our verdict
Worth it, if
- £22 per person below the typical fare on this route
- Lowest in 30 days on this route
- La Quinta Inn & Suites by Wyndham Chicago Downtown, rated 8 by 3,744 guests
The catch: Not nonstop: a stop on the way, 8h 59m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round-trip flights from San Antonio to Chicago are $430 per person, or $860 for two, for Oct 16–18, 2026 (2 nights), on Frontier with 1 stop. Highs run 58–65°F, with drizzle likely Friday and dry, overcast skies after that. The best-value hotel, La Quinta Inn & Suites by Wyndham Chicago Downtown, is $842 for the stay with breakfast included.
The total, before you go
£1,283 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £648 |
| La Quinta Inn & Suites by Wyndham Chicago Downtown, 2 nights, two guests, taxes in | £635 |
| The total, before you go | £1,283 |
| Hold luggage each, return (not in the total) | about £181 |
£22 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£324 per person, return
£648 for two, taxes and fees included · Frontier · 1 stop · 8h 59m
Out Fri, Oct 16, 10:03 AM – Fri, Oct 16, 7:02 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £324 | 1 stop | 8h 59m |
| American | £461 | nonstop | 3h |
| Y4 + VB | £453 | 1 stop | 27h |
Prices checked 13 Oct 2026, 16:14 GMT-5. Prices change; the binding price is the one on the booking site.
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Why now
At $430 per person, this fare is $29 below the typical fare on this route. That's a 6% gap, and it's the lowest price we've seen on this route in 30 days. We checked 12 offers for this weekend, and they ran from $430 to $651 per person. The American nonstop was $611. For two people, flights come to $860. Add the best-value hotel at $842 and $520 for food and fun, and the weekend totals $2,222. Mid-October falls between the summer beach season and the holiday markets, so this is a straightforward city weekend of museums, architecture, deep-dish and live blues. Highs run 58–65°F. Friday looks wet, with an 82% chance of drizzle, but Saturday and Sunday each show a 1% chance of rain under overcast skies. Prices are all-in as of when we checked, and they can change.
The kind of trip this is
This is a city weekend built around food, culture and nights out: skyscraper architecture, world-class museums, deep-dish pizza and blues clubs. It suits a couple or a pair of friends who like to walk a lot and eat well. The pace is full but easy, with one cool, cloudy day for museums and another for the river and the lakefront.
Weather in Chicago, 16 – 18 Oct
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 59 °F | 47 °F | 82% |
| Sat 17 Oct | 58 °F | 45 °F | 1% |
| Sun 18 Oct | 65 °F | 49 °F | 1% |
Where to stay in Chicago
All three picks are in The Loop, which puts architecture, theaters and Millennium Park right outside your door. La Quinta Inn & Suites by Wyndham Chicago Downtown is the best value at $842 for the stay ($421 a night). It scores 8 from 3,744 reviews, includes breakfast and has free cancellation. Canopy By Hilton Chicago Central Loop is the top-rated option at $960 ($480 a night) and scores 8.9 from 308 reviews. Heads-up: it's room only and doesn't offer free cancellation. Congress Plaza Hotel Chicago is the budget pick at $718 ($359 a night). It scores 7.1 from 4,532 reviews, it's room only and it has free cancellation. If nightlife matters most, River North has galleries, steakhouses and the city's main nightlife area.
La Quinta Inn & Suites by Wyndham Chicago Downtown
£635 for 2 nights, two guests · £317 a night
See roomsCanopy By Hilton Chicago Central Loop
£724 for 2 nights, two guests · £362 a night
See roomsCongress Plaza Hotel Chicago
£541 for 2 nights, two guests · £271 a night
See roomsAll hotels in Chicago for these dates
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Where in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise on dry, overcast Saturday.
- See the Bean and the fountains in Millennium Park, steps from all three hotels.
- Spend drizzly Friday evening or a slow morning at the Art Institute of Chicago.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Hear live blues at Kingston Mines on Saturday night.
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in San Antonio | San Antonio International (SAT) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 8h 59m (1 stop) |
| Distance | 1,053 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £648 |
| Hotel, 2 nights (La Quinta Inn & Suites by Wyndham Chicago Downtown) | £635 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,675 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: San Antonio to Chicago
| Per person | |
|---|---|
| This trip | £324 per person |
| Lowest in the last 30 days | £324 (13 Oct 2026) |
| Typical price, last 60 days | £346 |
| Price checks | 10 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed. It's a domestic trip, you'll pay in US dollars and there's no time difference.
- The outbound Frontier flight leaves SAT at 10:03 AM on Friday, Oct 16 and lands at O'Hare (ORD) at 7:02 PM, 8h 59m with 1 stop.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW). This fare lands at ORD.
- Free cancellation is available at La Quinta Inn & Suites by Wyndham Chicago Downtown and Congress Plaza Hotel Chicago, but not at Canopy By Hilton Chicago Central Loop.
- Pack a rain layer: Friday shows an 82% chance of drizzle and a low of 47°F.
Questions readers ask
How much is the flight?
When we checked, it was $430 per person round trip on Frontier, or $860 for two, with taxes and fees included. That's $29 below the typical fare on this route. Prices can change.
Is there a nonstop?
Yes. We found an American nonstop at $611 per person. It leaves at 7:10 AM and lands at 10:10 AM, 3 hours in the air. The $430 Frontier fare has 1 stop and takes 8h 59m.
What is the weather like?
Cool and cloudy. Friday has a high of 59°F with an 82% chance of drizzle. Saturday is overcast at 58°F, and Sunday is overcast at 65°F, both with a 1% chance of rain. Lows are 45–49°F.
Do I need a passport?
No. Chicago is a domestic trip from San Antonio, you'll pay in US dollars and both cities are on the same time.
Is 2 nights enough?
It's enough for a long weekend. You'd land Friday at 7:02 PM, so Saturday is your full day for the river cruise, Millennium Park and blues. Staying in The Loop keeps everything close.
What does the whole weekend cost for two?
We budgeted $2,222 for two people: $860 for flights, $842 for La Quinta Inn & Suites by Wyndham Chicago Downtown and $520 for spending.
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All trips from San Antonio · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License