Chicago from Tucson, Oct 23–25: round trip from $546
When we checked, a nonstop round trip on American from Tucson to Chicago was $546 per person ($1,092 for two) for Oct 23–25, 2026, a 2-night weekend. The forecast shows highs of 68–76°F with some drizzle. Hilton Chicago is the best-value hotel at $522 for the stay, or $261 a night.
The flight
$772 $546 per person, round trip
the typical fare on this route
$1,092 for two, taxes and fees included · American · nonstop · 3h 44m
Out Fri, Oct 23, 2:31 PM – Fri, Oct 23, 8:15 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American | $546 | nonstop | 3h 44m |
| American. Operated by Envoy Air as American Eagle | $556 | 1 stop | 5h 27m |
| American | $556 | 1 stop | 5h 10m |
Prices checked Oct 12, 2026, 11:33 AM 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 | $1,092 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,614 |
Regular: $2,066 You pay: $1,614 Saved: $452
the typical fare on this route.
Tweak this trip
Why go now
At $546 per person round trip, this fare is $339 below the highest fare we saw for these dates, a gap of 38%. We checked 12 fares for this weekend. They ran from $546 to $885 per person, and this nonstop on American is at the bottom of that range. For two, the flight comes to $1,092. Add Hilton Chicago and $520 of spending money and the whole weekend is $2,134. The forecast shows highs of 68–76°F and lows down to 51°F, with drizzle and rain chances between 19% and 33%. That's mild walking weather for late October, good for a river cruise, an afternoon at a museum and a long deep-dish dinner. The flight leaves Friday afternoon and lands in time for a late night out in River North.
The kind of trip this is
A city weekend built around food, architecture and live music. It suits a couple or two friends who like to walk a lot, eat well and stay out late at least one night. The pace is easy: one museum, one boat ride, one big pizza and one blues club, with the lakefront in between. You won't need a passport or a currency change, and the clock only moves 2 hours.
Weather in Chicago, Oct 23–25
Highs 57–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 76 °F | 67 °F | 33% |
| Sat, Oct 24 | 72 °F | 50 °F | 23% |
| Sun, Oct 25 | 57 °F | 49 °F | 19% |
Where to stay in Chicago
Hilton Chicago is the best value: $522 for the 2 nights ($261 a night) for a King Room, rated 7.9 from 981 reviews, in the Loop. Hilton Garden Inn Chicago Downtown South Loop is the budget pick on our list at $561 for the stay ($281 a night). It's also rated 7.9, from 486 reviews, and also in the Loop. Sable At Navy Pier Chicago, Curio Collection By Hilton is the top-rated option at 8.8 from 885 reviews. It costs $799 for the stay ($400 a night) and sits on the Near North Side by the lake. The Loop puts architecture, theatres and Millennium Park at your doorstep. Magnificent Mile / Streeterville is the area for Michigan Avenue shopping and lakefront hotels. Heads-up: all three rates are room only, with no free cancellation.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$683 for 2 nights, two guests · $342 a night
See roomsCongress Plaza Hotel Chicago
$550 for 2 nights, two guests · $275 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 to see the skyline from the water.
- See the Bean and the fountains in Millennium Park, a short walk from Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, then argue about which was better.
- Spend an afternoon at the Art Institute of Chicago if the drizzle shows up.
- Hear live blues at Kingston Mines on Saturday night.
- Catch a Cubs game at Wrigley Field if there's one on that weekend.
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Tucson | Tucson International (TUS) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 3h 44m nonstop |
| Distance | 1,444 miles each way |
| Time difference | +2 hours |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,092 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,134 |
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: Tucson to Chicago
| Per person | |
|---|---|
| This trip | $546 per person |
| Lowest in the last 30 days | $546 (Oct 12, 2026) |
| Typical price, last 60 days | $772 |
| Price checks | 9 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- Chicago is 2 hours ahead of Tucson, so plan for the time change.
- The nonstop takes 3h 44m. It leaves TUS at 2:31 PM and lands at ORD at 8:15 PM on Oct 23.
- Prices are all-in, with taxes and fees, as of when we checked. They can change before you book.
- All three hotel rates we found are room only, with no free cancellation.
Questions readers ask
How much is the flight?
When we checked, it was $546 per person round trip, or $1,092 for two, all-in. That's a nonstop on American. The next options we saw were $556 per person with one stop.
Do I need a passport?
No. It's a domestic trip, and you'll pay in US dollars the whole time.
What is the weather like?
The forecast shows highs of 72°F, 76°F and 68°F across the three days, with lows from 51°F to 65°F. Drizzle is in the mix, with rain chances of 19% to 33%, so bring a light rain jacket.
Is 2 nights enough?
For a first look, yes. You land at 8:15 PM Friday, which leaves Saturday and Sunday for the river cruise, the Art Institute, Millennium Park, deep-dish and a blues club. Save Wrigley Field and Lincoln Park for another trip.
Which airport do I fly into?
This fare lands at Chicago O'Hare International (ORD). The city also has Chicago Midway International (MDW). The flight covers 1,444 miles from Tucson International (TUS).
What does the whole weekend cost?
It comes to $2,134 for two: $1,092 for flights, $522 for Hilton Chicago and $520 of spending money, which works out to $130 per person per day.
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Chicago in pictures
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License