Chicago from Austin, 16 – 18 Oct: £1,213 for two, all in
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The verdict
Our verdict
Worth it, if
- Fare is $358 per person, $22 below the typical fare
- Saturday mostly clear, Sunday clear at 62°F, 1% rain chance
- Club Quarters scores 8.2 from 5,337 reviews, in The Loop
The catch: Frontier's fare has one stop and takes 6h 23m, while American's nonstop takes 2h 56m but costs $483 per person.
Worth it if a longer travel day for $358 per person suits you; skip it if you want the 2h 56m nonstop.
Worth it if you can live with one stop: $1,609 for two, all in, covers Frontier flights at $716 plus Club Quarters Hotel Central Loop, Chicago at $893, taxes and fees included. The trip runs Friday, Oct 16 to Sunday, Oct 18, 2026, for 2 nights, with one stop between Austin and O'Hare and 6h 23m of travel. Resort fees, a checked bag and spending money aren't in that total.
The total, before you go
£1,213 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £540 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £673 |
| The total, before you go | £1,213 |
| Hold luggage each, return (not in the total) | about £181 |
£17 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
£270 per person, return
£540 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 | £270 | 1 stop | 6h 23m |
| American | £364 | nonstop | 2h 56m |
| Frontier | £270 | 1 stop | 8h 4m |
Prices checked 12 Oct 2026, 19:38 GMT-5. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why now
At $358 per person, the fare is $22 below the typical fare on this route. That's 6% under the $380 we usually see, and it's the lowest fare in 30 days of our checks. Across the 12 offers we found, fares ran from $358 to $672 per person. The forecast starts with an overcast Friday at 56°F and a 60% chance of rain. After that, Saturday looks mostly clear at 52°F and Sunday looks clear at 62°F, both with a 1% chance of rain. That's good jacket weather for the river, the Loop and the museums. Chicago is on the same clock as Austin, so a two-night trip doesn't lose any time to jet lag. These prices were all in when we checked, and they can change before you book.
The kind of trip this is
This is a quick city weekend built around architecture seen from the river, a major art museum, deep-dish pizza and live blues at night. It suits a couple or two friends who like to walk, eat well and stay out a little late. The pace is full but easy: all three hotels are in The Loop, and the Friday flight lands at 6:31 PM, which leaves the evening open.
Weather in Chicago, 16 – 18 Oct
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 56 °F | 46 °F | 60% |
| Sat 17 Oct | 52 °F | 44 °F | 1% |
| Sun 18 Oct | 62 °F | 45 °F | 1% |
Where to stay in Chicago
All three are 4-star hotels in The Loop, with its architecture, theatres and Millennium Park close by. Our pick is Club Quarters Hotel Central Loop, Chicago, the hotel in the trip total: $893 for the 2 nights ($447 a night) and a score of 8.2 from 5,337 reviews. The top-rated option is Canopy By Hilton Chicago Central Loop at $962 ($481 a night), with an 8.9 from 308 reviews. On a tighter budget, Congress Plaza Hotel Chicago costs $750 ($375 a night) and scores 7.1 from 4,548 reviews. It's also the only one of the three with free cancellation. All three are room only. For dinner, West Loop has the restaurant row on Randolph Street, and River North is the center of the city's nightlife.
Club Quarters Hotel Central Loop, Chicago
£673 for 2 nights, two guests · £337 a night
See roomsCanopy By Hilton Chicago Central Loop
£725 for 2 nights, two guests · £363 a night
See roomsCongress Plaza Hotel Chicago
£565 for 2 nights, two guests · £283 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 clear 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 rainy-risk Friday evening or a slow morning at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if the schedule allows
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 | £540 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £673 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,605 |
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 | £270 per person |
| Lowest in the last 30 days | £270 (13 Oct 2026) |
| Typical price, last 60 days | £286 |
| Price checks | 6 |
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, you pay in US dollars and Chicago is on the same time as Austin.
- The outbound Frontier flight leaves Austin at 12:08 PM and lands at O'Hare at 6:31 PM after one stop.
- Resort fees and a checked bag aren't in the $1,609 total; we'd budget $520 in spending money for two.
- Only Congress Plaza Hotel Chicago offers free cancellation; the other two don't.
- Friday has a 60% chance of rain, so pack a light rain layer.
Questions readers ask
Is it worth it?
Yes, if you're fine with one stop. The fare is $358 per person, $22 below the typical fare on this route, and the weekend weather clears after Friday. If you'd rather fly nonstop, American's flight takes 2h 56m and costs $483 per person.
How much is the whole trip for two?
It's $1,609 all in: $716 for two round-trip Frontier fares plus $893 for 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included. Resort fees, a checked bag and spending money are extra.
What's the weather like?
Friday looks overcast, with a high of 56°F and a 60% chance of rain. Saturday looks mostly clear at 52°F, and Sunday looks clear at 62°F. Lows run 44°F to 46°F, so bring a jacket.
Is 2 nights enough?
It's enough for a city weekend. Friday's flight lands at 6:31 PM, which leaves Saturday and Sunday for the river cruise, Millennium Park, the Art Institute and deep-dish. It's a short trip, not a deep one.
Which airport do I fly into?
This Frontier fare flies from Austin-Bergstrom International (AUS) to Chicago O'Hare International (ORD). Chicago also has a second airport, Midway International (MDW), but this fare doesn't use it.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars and there's no time difference with Austin.
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All trips from Austin · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License