Chicago from Boise, 23 – 25 Oct: £1,042 for two, all in
This page’s text is in English for now; a translation is on its way.
The verdict
Our verdict
Worth it, if
- $430 per person, $68 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522
- Saturday high of 60°F with a 16% rain chance
The catch: The fare we priced has one stop and takes 8h 55m to get there, while the American nonstop takes 3h 47m but costs $539 per person.
Worth it if saving $68 per person is worth a long Friday of travel to you; skip it if two nights already feels too short.
Worth it if you don't mind a stop: $1,382 for two covers the flights at $860 plus Hilton Chicago at $522, with taxes and fees included, for Oct 23–25, 2026 (2 nights). You fly Alaska, operated by SkyWest Airlines as Alaska SkyWest, with one stop, and the outbound takes 8h 55m. Resort fees, a checked bag and spending money are not in the total.
The total, before you go
£1,042 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £648 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £1,042 |
| Hold luggage each, return (not in the total) | about £106 |
£51 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £26 each way per bag on Alaska, £106 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
£324 per person, return
£648 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 | £324 | 1 stop | 8h 55m |
| American | £406 | nonstop | 3h 47m |
| Alaska | £324 | 1 stop | 6h 41m |
Prices checked 12 Oct 2026, 18:34 GMT-6. 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
Tweak this trip
Why now
At $430 per person, this fare is $68 below the typical fare on this route, which is $498. That's a 14% gap, and it brings the trip to $1,382 for two with two nights at Hilton Chicago. Resort fees, a checked bag and spending money come on top. When we checked, round-trip fares on these dates ran from $430 to $717 per person, so this fare is at the bottom of that range. The forecast for late October looks mild. Friday reaches 71°F with a 29% chance of drizzle. Saturday is overcast at 60°F with a 16% rain chance, and Sunday tops out at 55°F. That's comfortable weather for a river cruise, an afternoon at a museum and a long deep-dish dinner. Prices change all the time, and none of these fares is held for you.
The kind of trip this is
This is a city weekend built around food, architecture and live music. Chicago is easy to see on foot: the towers of The Loop, the lakefront, the galleries of River North and a late set at a blues club. You can pack the days or keep them loose, and if the overcast days turn wet, the Art Institute is there. It suits couples and friends who like to eat well and stay out a little late.
Weather in Chicago, 23 – 25 Oct
Highs 55–71°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 71 °F | 57 °F | 29% |
| Sat 24 Oct | 60 °F | 53 °F | 16% |
| Sun 25 Oct | 55 °F | 48 °F | 23% |
Where to stay in Chicago
Hilton Chicago is our value pick and the hotel in the total. It's $522 for the 2 nights, or $261 a night, for a King Room in The Loop, and it scores 7.9 from 981 reviews. Heads-up: it doesn't offer free cancellation. Eurostars Magnificent Mile is the pick for reviews, scoring 8.7 from 2,285. It costs $773 for the stay ($387 a night) and comes with free cancellation. It's in River North, near the galleries, the steakhouses and the city's nightlife core. Congress Plaza Hotel Chicago costs $550 ($275 a night) for a Queen Room in The Loop, with free cancellation and a score of 7.1 from 4,548 reviews. The Loop puts architecture, theatres and Millennium Park right at your door. All three are room only, so breakfast isn't included.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsEurostars Magnificent Mile
£583 for 2 nights, two guests · £292 a night
See roomsCongress Plaza Hotel Chicago
£415 for 2 nights, two guests · £207 a night
See roomsAll hotels in Chicago for these dates
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
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 for the skyline from the water
- See the Bean and the fountains in Millennium Park, close to both Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend the overcast Sunday at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field
Also worth it
- Visit the Art Institute of Chicago
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
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 | £648 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,434 |
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 | £324 per person |
| Lowest in the last 30 days | £285 (13 Oct 2026) |
| Typical price, last 60 days | £375 |
| Price checks | 7 |
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).
- You don't need a passport, and you'll pay in US dollars.
- Chicago is 1 hour ahead of Boise.
- The outbound leaves Boise (BOI) at 8:25 AM and lands at Chicago O'Hare (ORD) at 6:20 PM, with one stop.
- Hilton Chicago doesn't offer free cancellation; Eurostars Magnificent Mile and Congress Plaza Hotel Chicago do.
- All three hotels are room only, and resort fees and a checked bag are not in the $1,382.
Questions readers ask
Is it worth it?
Worth it if you can live with a stop. The fare is $430 per person, $68 below the typical fare on this route, but the outbound takes 8h 55m. If time matters more to you than money, the American nonstop takes 3h 47m and costs $539 per person.
How much is the whole trip for two?
It's $1,382 for two: the flights at $860 plus Hilton Chicago at $522 for 2 nights, with taxes and fees included. Resort fees, a checked bag and spending money are extra. That's what we found when we checked, and prices can change.
What's the weather like?
Friday reaches 71°F with a 29% chance of drizzle. Saturday is overcast with a high of 60°F and a 16% rain chance. Sunday is overcast at 55°F, dropping to 48°F at night. Bring a light jacket.
Is 2 nights enough?
It's enough for a full Saturday. Because you land at 6:20 PM on Friday, plan on dinner that night, then the river cruise, Millennium Park and some blues on Saturday, with the Art Institute on Sunday.
Which hotel should we pick?
Hilton Chicago at $522 keeps the total at $1,382, but it has no free cancellation. If you want flexibility or higher scores, Eurostars Magnificent Mile is $773 and scores 8.7, and you can cancel for free.
Also found for you
The newest finds from Boise.
Just found · from BoiseLowest in 30 daysWorth it, if
San Francisco
14 – 21 Nov 2026 · 7 nights
- Nonstop on United, 2h 8m, leaving Boise at 8:15 AM
- $286 per person, $17 below the typical fare on this route
- Chelsea Inn near the Marina: 8.2 from 1,885 reviews, free cancellation
£1,723 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £431 + hotel £1,123 + resort fee £169, taxes in · a checked bag each adds about £121
United. Operated by SkyWest DBA United Express · nonstop · 2h 8m
The catch: Typical highs are only 58–62°F, with drizzle on Nov 14 and 18 and rain on Nov 20, and checked bags add about $160 for two.
Worth it if you want a walkable week of food and views in a light jacket; skip it if you need sunshine.
Tweak this trip
Just found · from BoiseNot worth it this week
Las Vegas
16 – 18 Oct 2026 · 2 nights
- Frontier nonstop, 1h 54m, leaving Boise at 2:50 PM Friday
- Highs 81–82°F with a 0% to 1% rain chance
- Excalibur at $327 for 2 nights, rated 7.7 from 30,748 reviews
£1,100 for two · 2 nights · flights, hotel, taxes & fees
Flights £853 + hotel £246, taxes in · a checked bag each adds about £181
Frontier · nonstop · 1h 54m
The catch: At $566 per person, the fare is above the $522 median of our earlier checks, and resort fees and a checked bag aren't in the total.
Worth it if Oct 16–18 is the only weekend you've got; skip it this week if your dates can move and you'd rather watch the fare.
Tweak this trip
Just found · from BoiseLowest in 30 daysWorth it, if
Big Island (Kona & Hilo)
14 – 21 Nov 2026 · 7 nights
- £153 per person below the typical fare on this route
- Lowest in 30 days on this route
- Kalani Kai#104, rated 9 by 6 guests
£1,726 for two · 7 nights · flights, hotel, taxes & fees
Flights £784 + hotel £942, taxes in · a checked bag each adds about £106
Alaska. Operated by Horizon Air as Alaska Horizon · with a stop · 19h 40m
The catch: Not nonstop: a stop on the way, 19h 40m in all.
Worth it if you want sun, sand and a pool; skip it if you want a city to walk.
Tweak this trip
More trips
Next weekend · from Boise
Las Vegas
23 – 25 Oct 2026 · 2 nights
- Nonstop on Frontier, 1h 54m
- £38 per person below the typical fare on this route
- Free cancellation at Horseshoe Las Vegas Hotel & Casino - A Caesars Rewards Destination
£1,033 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £645 + hotel £347 + resort fee £41, taxes in · a checked bag each adds about £181
Frontier · nonstop · 1h 54m
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want late nights and a crowd; skip it if you want to sleep.
The weekend after · from Boise
San Diego
30 Oct – 1 Nov 2026 · 2 nights
- Nonstop on Alaska. Operated by Horizon Air as Alaska Horizon, 2h 21m
- Free cancellation at Hilton Garden Inn San Diego Mission Valley/Stadium
- Typical highs 72–75°F, lows near 54°F this time of year
£905 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £620 + hotel £253 + resort fee £33, taxes in · a checked bag each adds about £106
Alaska. Operated by Horizon Air as Alaska Horizon · nonstop · 2h 21m
The catch: The best-value hotel is rated 7.6; a better one costs more.
Worth it if you want sun, sand and a pool; skip it if you want a city to walk.
Just found · from BoiseLowest in 30 daysWorth it, if
San Francisco
14 – 21 Nov 2026 · 7 nights
- Nonstop on United, 2h 8m, leaving Boise at 8:15 AM
- $286 per person, $17 below the typical fare on this route
- Chelsea Inn near the Marina: 8.2 from 1,885 reviews, free cancellation
£1,723 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £431 + hotel £1,123 + resort fee £169, taxes in · a checked bag each adds about £121
United. Operated by SkyWest DBA United Express · nonstop · 2h 8m
The catch: Typical highs are only 58–62°F, with drizzle on Nov 14 and 18 and rain on Nov 20, and checked bags add about $160 for two.
Worth it if you want a walkable week of food and views in a light jacket; skip it if you need sunshine.
All trips from Boise · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License