Chicago from San Antonio, Oct 23–25: $1,552 for two, all in
The verdict
Our verdict
Worth it, if
- $430 per person, $29 below the typical fare on this route
- Highs of 69–74°F with a 9–17% chance of rain
- Aloft by Marriott Chicago Mag Mile scores 8.1 from 2,535 reviews
The catch: The Frontier fare has one stop and the trip up takes 8h 59m, and checked bags run about $240 for two on top of the total.
Worth it if you'll trade a long travel day for the lower fare; skip it if a 2-night weekend calls for the 3h nonstop.
Worth it if you don't mind a long Friday of travel: $1,552 for two, all in. That's the Frontier flights at $860 plus 2 nights at Aloft by Marriott Chicago Mag Mile at $597 and its $95 property fee, with taxes and fees included. It runs Friday to Sunday, Oct 23–25, 2026, and the flight has one stop, leaving San Antonio at 10:03 AM and landing in Chicago at 7:02 PM.
The total, before you go
$1,552 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $860 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | $597 |
| Resort fee, collected at the desk | $95 |
| The total, before you go | $1,552 |
| 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); the resort fee is counted above. 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 23, 10:03 AM – Fri, Oct 23, 7:02 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $430 | 1 stop | 8h 59m |
| United | $631 | nonstop | 3h |
| Y4 + VB | $548 | 1 stop | 27h |
Prices checked Oct 15, 2026, 1:59 PM CDT. Prices change; the binding price is the one on the booking site.
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Why now
The fare is $430 per person, which is $29 below the typical fare on this route. That's 6% under the median of 16 earlier checks, and it's the lowest we've seen in 30 days. Across the 12 offers we checked, fares ran from $430 to $784 per person. The forecast for Oct 23–25 is highs of 69–74°F, lows of 59–61°F, overcast skies and a 9–17% chance of rain, so it's good walking weather for the river, the lakefront and Millennium Park. There's no passport to sort out, no currency to change and no time difference, since both cities are on the same clock. The big summer festivals are over and the holiday lights haven't gone up yet, which makes this a plain city weekend built around food, architecture and live music. Prices are what we found when we checked, and they can move.
The kind of trip this is
This is a city weekend that runs on food, architecture and live music. Expect deep-dish, a river cruise past the towers, an afternoon at the Art Institute and a blues club late on Saturday. It suits a couple or two friends who like to walk a lot and eat well. With 2 nights and a Friday evening arrival, Saturday is the full day, so the pace is quick and you'll want to plan around it.
Weather in Chicago, Oct 23–25
Highs 69–74°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 72 °F | 59 °F | 9% |
| Sat, Oct 24 | 74 °F | 61 °F | 11% |
| Sun, Oct 25 | 69 °F | 59 °F | 17% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile is the best value and the one in the total: $597 for the stay ($299 a night), plus a $95 property fee that's already counted, with a score of 8.1 from 2,535 reviews. It's in Streeterville, part of Magnificent Mile / Streeterville, which is good for shopping on Michigan Avenue and staying near the lake. Sable At Navy Pier Chicago, Curio Collection By Hilton is the top rated at 8.9 from 888 reviews, at $803 for the stay ($402 a night) plus $128 in fees at the property. Hilton Chicago puts you in The Loop, with its architecture, theatres and Millennium Park close by, for $608 ($304 a night) plus $97 at the property, and it scores 7.9 from 982 reviews. None of the three offers free cancellation at these rates.
Aloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 a night
See roomsSable At Navy Pier Chicago, Curio Collection By Hilton
$803 for 2 nights, two guests · $402 a night
See roomsHilton Chicago
$608 for 2 nights, two guests · $304 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 for the skyline from the water
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend an afternoon at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if one is on the schedule
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 (Aloft by Marriott Chicago Mag Mile) | $597 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,977 |
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 15, 2026) |
| Typical price, last 60 days | $459 |
| Price checks | 16 |
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 is needed: it's a domestic trip, prices are in US dollars, and there's no time difference.
- The flight is Frontier from San Antonio International (SAT) to Chicago O'Hare International (ORD), with one stop and 8h 59m.
- Checked bags aren't in the total and run about $240 for two.
- None of the three hotels offers free cancellation at the rates we found.
- Chicago is 1,053 miles from San Antonio, and Chicago Midway International (MDW) also serves the city.
Questions readers ask
Is it worth it?
It's worth it if you can live with the travel time. The fare is $29 per person below the typical fare on this route, and the forecast is mild. The catch is one stop and 8h 59m on Friday, so you'd land at 7:02 PM.
How much is the whole trip for two?
$1,552, all in. That's $860 for the Frontier flights plus $597 for 2 nights at Aloft by Marriott Chicago Mag Mile and its $95 property fee, with taxes and fees included. Checked bags (about $240 for two) and spending money aren't in that total.
Is there a nonstop?
Yes. When we checked, United had a nonstop leaving at 6:35 AM and landing at 9:35 AM, a 3h flight, at $631 per person. That's $1,262 for two, or $402 more than the Frontier fare.
What is the weather like?
The forecast is overcast all three days. Highs run from 69°F to 74°F, lows from 59°F to 61°F, and the chance of rain is 9% to 17%.
Is 2 nights enough?
It's enough for one full Saturday plus Sunday. With the Frontier flight landing at 7:02 PM on Friday, you'd pick a river cruise, the Art Institute, deep-dish and a blues club rather than trying to see everything.
Do I need a passport?
No. It's a domestic trip, prices are in US dollars, and Chicago is on the same time as San Antonio.
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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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