Chicago from Boise, Oct 23–25: round trip from $430
A round trip from Boise to Chicago costs $430 per person ($860 for two) for Oct 23–25, 2026. That's 2 nights on Alaska, operated by SkyWest Airlines as Alaska SkyWest, with one stop, and the forecast shows highs of 55–71°F with a small chance of rain. The best-value hotel, Hilton Chicago in The Loop, is $522 for the stay, or $261 a night.
The flight
$498 $430 per person, round trip
the typical fare on this route
$860 for two, taxes and fees included · Alaska. Operated by SkyWest Airlines as Alaska SkyWest · 1 stop · 8h 55m
Out Fri, Oct 23, 8:25 AM – Fri, Oct 23, 6:20 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Alaska. Operated by SkyWest Airlines as Alaska SkyWest | $430 | 1 stop | 8h 55m |
| American | $539 | nonstop | 3h 47m |
| Alaska | $430 | 1 stop | 6h 41m |
Prices checked Oct 12, 2026, 6:34 PM MDT. 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 | $860 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,382 |
Regular: $1,518 You pay: $1,382 Saved: $136
the typical fare on this route.
Tweak this trip
Why go now
At $430 per person round trip, this fare is $68 below the typical fare on this route. That's 14% under the $498 our earlier checks usually turned up. For two people it comes to $860, all-in with taxes and fees, as found when we checked. Fares move, so take it as a snapshot. Across the 12 offers we saw for this weekend, prices ran from $430 to $717 per person. Late October falls between Chicago's summer festivals and its holiday markets. The forecast shows 71°F on Friday, 60°F on Saturday and 55°F on Sunday, with rain chances between 16% and 29%. That's jacket weather, which suits museums, a river cruise and long dinners. Add Hilton Chicago at $522 for both nights and a $520 spending budget, and the whole weekend for two comes to $1,902.
The kind of trip this is
This is a city weekend built around food, architecture and music. Two nights is enough for a river cruise, one big museum, a deep-dish dinner and a blues set, and the pace stays easy if you base yourself in one area and walk it. It suits couples and friends who want a fall getaway with good restaurants and a skyline, and you don't need a passport.
Weather in Chicago, Oct 23–25
Highs 55–71°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 71 °F | 57 °F | 29% |
| Sat, Oct 24 | 60 °F | 53 °F | 16% |
| Sun, Oct 25 | 55 °F | 48 °F | 23% |
Where to stay in Chicago
Hilton Chicago is the best-value pick: a King Room costs $522 for both nights ($261 a night), with a 7.9 review score from 981 reviews. It's in The Loop, which puts the architecture, the theatres and Millennium Park at your doorstep. Congress Plaza Hotel Chicago is also in The Loop and is listed as the budget pick. A Queen Room there is $550 for the stay ($275 a night), with a 7.1 score from 4,548 reviews and free cancellation. Eurostars Magnificent Mile is the top rated of the three, scoring 8.7 from 2,285 reviews, at $773 for the stay ($387 a night) with free cancellation. It's in River North, the city's nightlife core, with galleries and steakhouses nearby. All three rates are room only, and the Hilton rate can't be cancelled for free.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsEurostars Magnificent Mile
$773 for 2 nights, two guests · $387 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, right by The Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, and come hungry.
- Visit the Art Institute of Chicago, a good plan for an overcast 60°F Saturday.
- Hear live blues at Kingston Mines on Friday or Saturday night.
Also worth it
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Boise | Boise Airport (BOI) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 8h 55m (1 stop) |
| Distance | 1,448 miles each way |
| Time difference | +1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $860 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,902 |
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: Boise to Chicago
| Per person | |
|---|---|
| This trip | $430 per person |
| Lowest in the last 30 days | $378 (Oct 13, 2026) |
| Typical price, last 60 days | $498 |
| Price checks | 7 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- It's a domestic trip, so you don't need a passport, and you'll pay in US dollars.
- Chicago is 1 hour ahead of Boise, and the trip covers 1,448 miles.
- The $430 fare has one stop. It leaves Boise at 8:25 AM on Friday, Oct 23 and lands at Chicago O'Hare (ORD) at 6:20 PM, 8h 55m in total.
- American flies nonstop for $539 per person, leaving at 3:24 PM and landing at 8:11 PM, 3h 47m in total.
- All three hotel rates are room only. Eurostars Magnificent Mile and Congress Plaza Hotel Chicago offer free cancellation; Hilton Chicago doesn't.
Questions readers ask
How much is the flight?
It's $430 per person round trip, or $860 for two, on Alaska with one stop. That's all-in, as found when we checked, and $68 below the $498 typical fare on this route. Prices can change before you book.
Is there a nonstop option?
Yes. American flies nonstop for $539 per person, or $1,078 for two. It leaves Boise at 3:24 PM on Friday and lands at 8:11 PM, 3h 47m in total.
What is the weather like?
Friday is forecast at 71°F with a 29% chance of drizzle. Saturday is overcast at 60°F, and Sunday is overcast at 55°F. Lows run 48–57°F, so pack a jacket.
Is 2 nights enough?
It's enough for a first visit. The one-stop fare lands at 6:20 PM on Friday, which leaves Saturday as your full day for the river cruise, the Art Institute and Millennium Park. Save the nights for deep-dish and live blues.
What does the whole weekend cost for two?
It comes to about $1,902 for two: $860 for flights, $522 for two nights at Hilton Chicago and $520 for food and spending, which works out to $130 per person per day.
Do I need a passport?
No. Chicago is a domestic trip from Boise, and you'll pay in US dollars.
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Chicago in pictures
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Image credits
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- Photo: Joshua Santos / Pexels, Pexels License