Chicago from Phoenix, Oct 16–18: round trip from $420
A round trip from Phoenix to Chicago costs $420 per person ($840 for two) on Frontier for Oct 16–18, 2026, a 2-night weekend. That fare has one stop, and Frontier also had a nonstop at $425 per person. Expect highs of 53–62°F with drizzle possible Friday and clear skies after, and the best-value hotel is $917 for the stay.
The flight
$420 per person, round trip
$840 for two, taxes and fees included · Frontier · 1 stop · 6h 13m
Out Fri, Oct 16, 4:18 PM – Sat, Oct 17, 12:31 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $420 | 1 stop | 6h 13m |
| Frontier | $425 | nonstop | 3h 27m |
| Frontier | $448 | 1 stop | 14h 6m |
Prices checked Oct 12, 2026, 12:01 PM MST. 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 | $840 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights | $917 |
| Trip total for two | $1,757 |
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Why go now
At $420 per person, this fare is $7 below the $427 median of our 6 earlier checks on this route, a 2% gap. That's modest, and the low across those checks was $414, so think of it as a fair price rather than a steal. Frontier also had a nonstop at $425 per person that takes 3h 27m instead of 6h 13m, which we'd call worth it. The forecast helps: Saturday, Oct 17 looks clear with a high of 53°F, and Sunday warms to 62°F with a 2% chance of rain. Friday shows a 51% chance of drizzle, but you land after midnight. Mid-October means jacket weather, good for museums, the river and long pizza dinners. Prices are all-in as we found them and can change before you book.
The kind of trip this is
This is a city weekend built around architecture, museums, pizza and live music, at a steady but unhurried pace. It suits a couple or a pair of friends who like walking a city and eating well, with cool, mostly dry days that call for layers. With a late Friday arrival, the trip really comes down to Saturday and Sunday, so pick a few things and leave room for a long dinner.
Weather in Chicago, Oct 16–18
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 57 °F | 46 °F | 51% |
| Sat, Oct 17 | 53 °F | 45 °F | 2% |
| Sun, Oct 18 | 62 °F | 46 °F | 2% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago is the best-value pick: $917 for the 2 nights ($459 a night) in a Standard Queen Room, rated 8.2 from 5,337 reviews. River Hotel is the top rated at 8.3 from 7,925 reviews, $994 for the stay ($497 a night) in a Small Queen Room. Both are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep, and neither offers free cancellation. The budget choice is Hotel Chicago West Loop, SureStay Collection by Best Western at $685 for the stay ($343 a night), rated 7.4 from 877 reviews, and it does come with free cancellation. West Loop is the one for food, with converted warehouses and the restaurant row on Randolph Street. All three rates are room only.
Club Quarters Hotel Central Loop, Chicago
$917 for 2 nights, two guests · $459 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsHotel Chicago West Loop, SureStay Collection by Best Western
$685 for 2 nights, two guests · $343 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 while Saturday, Oct 17 is forecast clear.
- See the Bean and the fountains in Millennium Park, a short walk from the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, then settle the argument yourselves.
- Spend a few hours at the Art Institute of Chicago, a solid plan in any weather.
- 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 Phoenix | Phoenix Sky Harbor International (PHX), Phoenix-Mesa Gateway (AZA) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 6h 13m (1 stop) |
| Distance | 1,452 miles each way |
| Time difference | +2 hours |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $840 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $917 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,277 |
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: Phoenix to Chicago
| Per person | |
|---|---|
| This trip | $420 per person |
| Lowest in the last 30 days | $414 (Oct 12, 2026) |
| Typical price, last 60 days | $427 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed: it's a domestic trip, and you pay in US dollars.
- Chicago is 2 hours ahead of Phoenix, so the 4:18 PM departure lands at 12:31 AM local time on Saturday, Oct 17.
- The $420 fare is a one-stop Frontier trip of 6h 13m from PHX to Chicago O'Hare International (ORD), 1,452 miles.
- Only Hotel Chicago West Loop, SureStay Collection by Best Western has free cancellation on the rate we found.
- Our weekend budget for two comes to $2,277: $840 flights, $917 hotel and $520 for spending.
Questions readers ask
How much is the flight?
We found $420 per person round trip, $840 for two, on Frontier with one stop, all-in with taxes and fees when we checked. A Frontier nonstop was $425 per person, $850 for two, leaving at 7:32 PM and landing at 12:59 AM. Prices can change.
Is $420 a good price for this route?
It's fair. The median of our 6 earlier checks on this route was $427, so this fare is $7 below that, or 2%. The low across those checks was $414.
Do I need a passport?
No. Chicago is a domestic trip from Phoenix, and the currency is the US dollar. Just set your watch 2 hours ahead.
What is the weather like?
Friday, Oct 16 has a high of 57°F and a 51% chance of drizzle. Saturday is clear at 53°F and Sunday is clear at 62°F, both with a 2% chance of rain. Lows sit around 45°F to 46°F, so pack a warm layer.
Is 2 nights enough?
For a city break, yes, if you plan around it. The one-stop flight lands at 12:31 AM Saturday, so your full days are Saturday and Sunday. That's enough for the river cruise, Millennium Park, the Art Institute and a deep-dish dinner.
What does the whole weekend cost?
We put it at $2,277 for two: $840 for flights, $917 for Club Quarters Hotel Central Loop, Chicago and $520 for spending, which works out to $130 per person per day.
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License