Chicago from San Antonio, Oct 16–18: $1,702 for two, all in
The verdict
Our verdict
Worth it, if
- 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
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.
Worth it if you can live with one stop: $1,702 for two covers Frontier flights at $860 plus 2 nights at La Quinta Inn & Suites by Wyndham Chicago Downtown at $842, with taxes and fees included and checked bags and spending money extra. You leave Friday, Oct 16 and come back Sunday, Oct 18, 2026. The Frontier outbound isn't nonstop: it has one stop, leaves San Antonio at 10:03 AM and takes 8h 59m.
The total, before you go
$1,702 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $860 |
| La Quinta Inn & Suites by Wyndham Chicago Downtown, 2 nights, two guests, taxes in | $842 |
| The total, before you go | $1,702 |
| A checked bag each, round trip (not in the total) | about $240 |
$29 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); 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
$430 per person, round trip
$860 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 | $430 | 1 stop | 8h 59m |
| American | $611 | nonstop | 3h |
| Y4 + VB | $601 | 1 stop | 27h |
Prices checked Oct 13, 2026, 4:14 PM CDT. Prices change; the binding price is the one on the booking site.
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Why now
At $430 per person, the Frontier fare is $29 below the typical fare on this route, or 6% under, and it carries a Lowest in 30 days badge from our checks. Across 12 offers we saw for these dates, fares ran from $430 to $651 per person. The whole trip comes to $1,702 for two, flights plus 2 nights at La Quinta, taxes and fees included. Bags, any resort fees and spending money come on top, and our budget sets aside $520 for spending, which makes $2,222 in all. Mid-October here means jacket weather. Friday brings drizzle, with an 82% chance of rain and a high of 59°F. Saturday and Sunday look overcast and dry, with highs of 58°F and 65°F. That works for the Art Institute, a river cruise and deep-dish. Prices were current when we checked and can change.
The kind of trip this is
This is a city weekend for two: architecture, museums, deep-dish and blues, mostly in and around The Loop. The pace is easy. Friday mostly goes to getting there, which leaves two dry days to walk the river, Millennium Park and the Art Institute. It suits couples or friends who care more about food and culture than beaches and don't mind arriving on Friday evening.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 47 °F | 82% |
| Sat, Oct 17 | 58 °F | 45 °F | 1% |
| Sun, Oct 18 | 65 °F | 49 °F | 1% |
Where to stay in Chicago
All three hotels are in the Chicago Loop, which puts The Loop's architecture, theaters and Millennium Park at your doorstep. La Quinta Inn & Suites by Wyndham Chicago Downtown is our best-value pick and the one in the total: $842 for 2 nights ($421 a night) for a larger king room with a sofa bed. Breakfast and free cancellation are included, and 3,744 guests rate it 8. Canopy By Hilton Chicago Central Loop is the top rated at 8.9 from 308 reviews. It costs $960 for the stay ($480 a night), room only, with no free cancellation. Congress Plaza Hotel Chicago is the budget choice at $718 ($359 a night), rated 7.1 by 4,532 guests, room only with free cancellation. For nightlife, River North is the city's core, and West Loop has its restaurant row on Randolph Street.
La Quinta Inn & Suites by Wyndham Chicago Downtown
$842 for 2 nights, two guests · $421 a night
See roomsCanopy By Hilton Chicago Central Loop
$960 for 2 nights, two guests · $480 a night
See roomsCongress Plaza Hotel Chicago
$718 for 2 nights, two guests · $359 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 the Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend drizzly hours at the Art Institute of Chicago
- Hear live blues at Kingston Mines
- Catch a Cubs game at Wrigley Field
Also worth it
- Visit the Art Institute of Chicago
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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 | $860 |
| Hotel, 2 nights (La Quinta Inn & Suites by Wyndham Chicago Downtown) | $842 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,222 |
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 | $430 per person |
| Lowest in the last 30 days | $430 (Oct 13, 2026) |
| Typical price, last 60 days | $459 |
| Price checks | 10 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, you pay in US dollars and there's no time difference from San Antonio.
- The Frontier outbound leaves at 10:03 AM, lands at O'Hare (ORD) at 7:02 PM and has one stop.
- An American nonstop leaves at 7:10 AM and takes 3h, at $611 per person.
- Fares include taxes and fees, but a checked bag is about $240 for two and isn't included.
- Chicago is served by both O'Hare (ORD) and Midway (MDW).
Questions readers ask
Is it worth it?
Worth it if you pack light and don't mind the stop. The fare is 6% under the typical fare on this route, and the hotel in the total includes breakfast and free cancellation. If your time matters more, the outbound takes 8h 59m.
How much is the whole trip for two?
It's $1,702 for two, taxes and fees included: $860 for the flights plus $842 for 2 nights at La Quinta Inn & Suites by Wyndham Chicago Downtown. A checked bag (about $240 for two) and spending money are extra. Our budget allows $520 for spending.
Is there a nonstop?
Yes. American has a nonstop that leaves at 7:10 AM and lands at 10:10 AM, but it's $611 per person, or $1,222 for two, compared with $430 per person on Frontier with one stop.
What is the weather like?
Friday shows drizzle, an 82% chance of rain and a high of 59°F. Saturday is overcast at 58°F and Sunday is overcast at 65°F, each with a 1% chance of rain. Lows run from 45°F to 49°F, so bring a jacket.
Is 2 nights enough?
For a Loop weekend, yes. You land at 7:02 PM Friday, which leaves Saturday and Sunday for a river cruise, Millennium Park, the Art Institute and deep-dish. All of those are close to the three hotels we picked.
Do I need a passport?
No. It's a domestic trip of 1,053 miles, you pay in US dollars and Chicago is on the same time as San Antonio.
Also found for you
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Oct 23–25, 2026 · 2 nights
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Tweak this trip
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Nov 13–17, 2026 · 4 nights
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The catch: The Frontier fare has 1 stop, takes 13h 48m and lands at 5:32 AM, and a checked bag is about $240 for two.
Worth it if saving matters more than sleep; skip it and look at the $660 Southwest nonstop if you want to arrive rested.
Tweak this trip
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San Francisco
Nov 13–17, 2026 · 4 nights
- $209 per person, $170 below the highest fare we saw for these dates
- Free cancellation at FOUND Hotel Carlton, Nob Hill, rated 7.8 from 3,184 reviews
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$1,236 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights $418 + hotel $711 + resort fee $107, taxes in · a checked bag each adds about $240
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The catch: The $209 fare is a Frontier red-eye with one stop, 11h 50m in total, and a checked bag is about $240 for two.
Worth it if you can sleep on a red-eye and want the city on foot; skip it if you'd rather pay $758 for two for United's 4h 2m nonstop.
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