Chicago from Austin, Oct 16–18: round trip from $358
When we checked, a round trip from Austin to Chicago on Frontier was $358 per person, or $716 for two, for Oct 16–18, 2026 (2 nights). The flight has one stop, and a nonstop on American was $483 per person. Highs run 52–62°F with only Friday looking wet, and our best-value hotel pick is $893 for the stay.
The flight
$380 $358 per person, round trip
the typical fare on this route
$716 for two, taxes and fees included · Frontier · 1 stop · 6h 23m
Out Fri, Oct 16, 12:08 PM – Fri, Oct 16, 6:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $358 | 1 stop | 6h 23m |
| American | $483 | nonstop | 2h 56m |
| Frontier | $358 | 1 stop | 8h 4m |
Prices checked Oct 12, 2026, 7:38 PM CDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $716 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights | $893 |
| Trip total for two | $1,609 |
Regular: $1,653 You pay: $1,609 Saved: $44
the typical fare on this route.
Tweak this trip
Why go now
$358 per person round trip is $22 below the typical fare on this route, about 6% under, and it carries the Lowest in 30 days tag. We checked 12 offers, and fares ran from $358 to $672. Here's the trade-off: Frontier makes one stop. You leave Austin at 12:08 PM on Friday, Oct 16 and land at O'Hare at 6:31 PM. For Saturday the forecast says mostly clear and 52°F, and Sunday looks clear at 62°F. Friday is overcast with a 60% chance of rain, so plan that first evening indoors. Mid-October falls between the summer festivals and the holiday markets, which makes it a good weekend for architecture, museums and deep-dish. For two people, flights, the best-value hotel and $520 for spending add up to $2,129.
The kind of trip this is
This is a city weekend built around food, architecture, museums and live music. It suits a couple or a pair of friends who like to walk a lot and eat well. You arrive Friday evening, so Saturday and Sunday do the work. That's enough time for a river cruise, an afternoon at the Art Institute, a deep-dish dinner and one late night of blues. Bring a warm layer for 44–46°F evenings.
Weather in Chicago, Oct 16–18
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 60% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
All three picks are 4-star hotels in The Loop, which puts the architecture, the theatres and Millennium Park right outside your door. Club Quarters Hotel Central Loop, Chicago is the best value: $893 for the 2 nights ($447 a night) for a Club Room, rated 8.2 across 5,337 reviews. Canopy By Hilton Chicago Central Loop is the top rated at 8.9 from 308 reviews, $962 for the stay or $481 a night. Congress Plaza Hotel Chicago is the budget pick at $750 total ($375 a night), rated 7.1 from 4,548 reviews. It's also the only one of the three with free cancellation. All three rates are room only. For nightlife, River North is a short hop from The Loop. For dinner, try the West Loop's restaurant row on Randolph Street.
Club Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 a night
See roomsCanopy By Hilton Chicago Central Loop
$962 for 2 nights, two guests · $481 a night
See roomsCongress Plaza Hotel Chicago
$750 for 2 nights, two guests · $375 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, ideally on Saturday when the sky looks mostly clear
- See the Bean and the fountains in Millennium Park, a short walk from all three hotels
- Eat deep-dish at Lou Malnati's or Pequod's, a good plan for rainy Friday night
- Spend a few hours 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 that weekend
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Austin | Austin-Bergstrom International (AUS) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 6h 23m (1 stop) |
| Distance | 980 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $716 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $893 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,129 |
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: Austin to Chicago
| Per person | |
|---|---|
| This trip | $358 per person |
| Lowest in the last 30 days | $358 (Oct 13, 2026) |
| Typical price, last 60 days | $380 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- You don't need a passport. Chicago is in the same time zone as Austin and uses the US dollar.
- The $358 Frontier fare has one stop and takes 6h 23m, covering 980 miles from AUS to O'Hare (ORD).
- The prices include taxes and fees as we found them, and they can change before you book.
- All three hotel rates are room only, and only Congress Plaza Hotel Chicago offers free cancellation.
- The forecast has lows of 44–46°F, and Friday has a 60% chance of rain.
Questions readers ask
How much is the flight?
When we checked, Frontier was $358 per person round trip, $716 for two, with taxes and fees included. That's $22 below the typical fare on this route. Prices can move before you book.
Is there a nonstop?
Yes. American had a nonstop for $483 per person that leaves at 6:00 AM and lands at 8:56 AM, which is 2h 56m. The Frontier fare has one stop and takes 6h 23m, arriving at 6:31 PM.
What is the weather like?
Friday, Oct 16 looks overcast at 56°F with a 60% chance of rain. Saturday is mostly clear at 52°F, and Sunday is clear at 62°F. Lows are 44–46°F, so bring a jacket.
Do I need a passport?
No. It's a domestic trip, there's no time difference from Austin, and you pay in US dollars.
Is 2 nights enough?
For a first look, yes. Since you land Friday evening, Saturday and Sunday cover a river cruise, Millennium Park, the Art Institute, deep-dish and a night at Kingston Mines. Our estimate for two is $2,129, which includes $520 for spending.
Which hotel should I pick?
Club Quarters Hotel Central Loop, Chicago is the best value at $893 for the stay. Canopy By Hilton Chicago Central Loop has the top rating at 8.9. Congress Plaza Hotel Chicago costs the least at $750 and has free cancellation.
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Chicago in pictures
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