Asheville from Chicago, 16 – 18 Oct: £1,155 for two, all in
The verdict
Our verdict
Worth it, if
- Free cancellation at Brookstone Lodge near Biltmore Village, an Ascend Collection Hotel
- Highs 60–80°F, little rain expected
- No passport needed
The catch: Not nonstop: 2 stops on the way, 42h 48m in all.
Worth it if you want to be outside all day; skip it if you want to lie by a pool.
Asheville is 2 nights from Chicago, 16 – 18 Oct 2026. The cheapest round trip we found is £383 per person (F9 + G4, 2 stops, 42h 48m). Hotels start at £195 a night; Highs 60–80°F, little rain expected.

The total, before you go
£1,155 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £765 |
| Brookstone Lodge near Biltmore Village, an Ascend Collection Hotel, 2 nights, two guests, taxes in | £390 |
| The total, before you go | £1,155 |
| Hold luggage each, return (not in the total) | about £181 |
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
£383 per person, return
£765 for two, taxes and fees included · F9 + G4 · 2 stops · 42h 48m
Out Fri, Oct 16, 8:11 PM – Sat, Oct 17, 10:25 PM · back Sun, Oct 18, 7:50 AM – Mon, Oct 19, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| F9 + G4 | £383 | 2 stops | 42h 48m |
| F9 + G4 | £397 | 1 stop | 36h 17m |
| F9 + G4 | £430 | 2 stops | 31h 44m |
Prices checked 13 Oct 2026, 12:30 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
Tweak this trip
Why Asheville
Why we picked it: Asheville is the best value we priced for the weekend: $508 round trip, 5% under the typical price.
Asheville mixes the Biltmore Estate and the Blue Ridge Parkway with one of the densest craft-brewery scenes in the country and a creative mountain-town spirit.
Weather in Asheville, 16 – 18 Oct
Highs 60–80°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 80 °F | 47 °F | 13% |
| Sat 17 Oct | 62 °F | 37 °F | 5% |
| Sun 18 Oct | 60 °F | 37 °F | 0% |
Where to stay in Asheville
Brookstone Lodge near Biltmore Village, an Ascend Collection Hotel
£390 for 2 nights, two guests · £195 a night
See roomsCambria Hotel Downtown Asheville
£956 for 2 nights, two guests · £478 a night
See roomsComfort Inn Biltmore West
£397 for 2 nights, two guests · £199 a night
See roomsAll hotels in Asheville 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 Asheville
- Downtown Asheville: Art Deco streets with breweries, music venues and galleries on foot.
- Biltmore Village: Inns and shops at the gates of the Biltmore Estate.
- River Arts District: Converted mills with studios and riverside restaurants.
- West Asheville: Local bars and cafes along Haywood Road.
- Black Mountain: Small mountain town 15 miles east with craft shops and trailheads.
What to do in Asheville
Signature experiences
- Tour the Biltmore Estate and its gardens
- Drive the Blue Ridge Parkway to Craggy Gardens
- Tour the breweries from Wicked Weed to Sierra Nevada
- Hear bluegrass at the Grey Eagle or the Orange Peel
- Hike to Catawba Falls or Mount Mitchell
- Eat your way through the River Arts District
Tours and tickets in Asheville
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 Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in Asheville | Asheville Regional (AVL) |
| Flight time | 42h 48m (2 stops) |
| Distance | 513 miles each way |
| Time difference | +1 hour |
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
What 2 nights in Asheville costs
| Estimate | |
|---|---|
| Flights for two | £766 |
| Hotel, 2 nights (Brookstone Lodge near Biltmore Village, an Ascend Collection Hotel) | £390 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,547 |
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: Chicago to Asheville
| Per person | |
|---|---|
| This trip | £383 per person |
| Lowest in the last 30 days | £363 (13 Oct 2026) |
| Typical price, last 60 days | £400 |
| Price checks | 20 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Asheville.
- Currency: US dollar (USD).
- Peak fall foliage on the Parkway and the busiest weekends
Questions readers ask
How much does 2 nights in Asheville from Chicago cost?
About £1,547 for two: £766 in flights, £390 for the hotel and £392 for food, getting around and tickets.
What is the weather like in Asheville 16 – 18 Oct?
Highs 60–80°F, little rain expected
Do I need a passport for Asheville?
No. No passport needed for travellers from the United States: a government photo ID is enough for Asheville.
How long is the flight from Chicago to Asheville?
42h 48m with 2 stops on F9 + G4, on the fare we found.
Is £383 a good price for Chicago to Asheville?
It is 4% below the typical £400 per person we see on this route, which is why it made the list.
Also found for you
The newest finds from Chicago.
Just found · from ChicagoNot worth it this week
Asheville
23 – 25 Oct 2026 · 2 nights
- Clear skies Friday and Saturday, highs of 69°F and 71°F
- Comfort Suites Outlet Center: 8.2 from 556 reviews, breakfast included
- October is peak fall foliage on the Blue Ridge Parkway
£1,192 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £794 + hotel £357 + resort fee £41, taxes in · a checked bag each adds about £181
F9 + G4 · with a stop · 39h 13m
The catch: The $527 fare has 2 stops and takes 39h 13m, landing Saturday at 6:00 PM, and a checked bag is about $240 for two.
Worth it if you switch to the $579 nonstop and want foliage and breweries; skip this 2-stop fare if you want a real weekend.
Tweak this trip
Just found · from ChicagoLowest in 30 daysWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- $366 per person, $37 below the typical fare on this route
- Breakfast included at Sonesta Select, rated 8.7 from 2,186 reviews
- Highs of 71–85°F with rain chances of 20% or less
£898 for two · 2 nights · flights, hotel, taxes & fees
Flights £552 + hotel £347, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 42m
The catch: The Frontier outbound has one stop and takes 12h 42m, leaving 8:11 PM Friday and landing 8:53 AM Saturday.
Worth it if you want a Saturday of honky-tonks and hot chicken for less; skip it if you need a full Friday night in town.
Tweak this trip
Just found · from ChicagoWorth it, if
Cancún
14 – 21 Nov 2026 · 7 nights
- Nonstop from O'Hare: leave 6:10 AM, land in Cancún 11:08 AM
- Aloft by Marriott Cancun: 8.1 from 798 reviews, free cancellation
- $404 per person, right at the $404 median of 13 checks
£1,207 for two · 7 nights · flights, hotel, taxes & fees
Flights £608 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · nonstop · 7h 59m
The catch: Weather normals for these dates show drizzle most days and rain on two, and a checked bag is about $240 for two, not in the total.
Worth it if you want a warm, easy beach week at a fair fare; skip it if gray, drizzly days would spoil the trip for you.
Tweak this trip
More trips
Next weekend · from ChicagoWorth it, if
Orlando
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, ORD to MCO in 2h 57m
- $280 per person, $10 under the typical $290 on this route
- Breakfast included at a hotel rated 8 from 4,289 reviews
£616 for two · 2 nights · flights, hotel, taxes & fees
Flights £422 + hotel £194, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 57m
The catch: You land just after midnight, so this is really a Saturday and Sunday, and a checked bag is about $240 for two, which isn't in the total.
Worth it if the two of you want one big park day on a short budget; skip it if you want a slow, unhurried vacation.
The weekend after · from Chicago21% below typicalWorth it, if
Great Smoky Mountains
23 – 25 Oct 2026 · 2 nights
- $429 per person, $118 below the typical fare on this route
- Zoders Inn and Suites in Gatlinburg, 8.2 from 1,812 reviews
- Peak fall foliage, highs of 59–66°F, 10% rain Friday and Saturday
£861 for two · 2 nights · flights, hotel, taxes & fees
Flights £647 + hotel £214, taxes in · a checked bag each adds about £106
Delta · with a stop · 4h 27m
The catch: The $429 fare has one stop and leaves O'Hare at 5:27 AM, and late October brings the busiest weekends of the year.
Worth it if you want fall color and mountain trails for a weekend and don't mind crowds; skip it if you need a quiet park.
A week away · from ChicagoLowest in 30 daysWorth it, if
New York City
14 – 21 Nov 2026 · 7 nights
- $244 per person, $104 below the typical fare on this route
- Pod 51 scores 8.2 from 9,513 reviews, with free cancellation
- Met or MoMA mornings, highs of 45–55°F for walking the High Line
£1,574 for two · 7 nights · flights, hotel, taxes & fees
Flights £368 + hotel £1,206, taxes in · a checked bag each adds about £181
Frontier · with a stop · 9h 30m
The catch: The Frontier fare has one stop and takes 9h 30m, and Pod 51's room is a bunk pod with a shared bathroom.
Worth it if a long travel day and a bunk pod are fine for a week in New York; skip it if you need a private bathroom.
Just found · from ChicagoLowest in 30 daysWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- $366 per person, $37 below the typical fare on this route
- Breakfast included at Sonesta Select, rated 8.7 from 2,186 reviews
- Highs of 71–85°F with rain chances of 20% or less
£898 for two · 2 nights · flights, hotel, taxes & fees
Flights £552 + hotel £347, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 42m
The catch: The Frontier outbound has one stop and takes 12h 42m, leaving 8:11 PM Friday and landing 8:53 AM Saturday.
Worth it if you want a Saturday of honky-tonks and hot chicken for less; skip it if you need a full Friday night in town.
Just found · from ChicagoWorth it, if
Cancún
14 – 21 Nov 2026 · 7 nights
- Nonstop from O'Hare: leave 6:10 AM, land in Cancún 11:08 AM
- Aloft by Marriott Cancun: 8.1 from 798 reviews, free cancellation
- $404 per person, right at the $404 median of 13 checks
£1,207 for two · 7 nights · flights, hotel, taxes & fees
Flights £608 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · nonstop · 7h 59m
The catch: Weather normals for these dates show drizzle most days and rain on two, and a checked bag is about $240 for two, not in the total.
Worth it if you want a warm, easy beach week at a fair fare; skip it if gray, drizzly days would spoil the trip for you.
All trips from Chicago · Asheville from every city · Prices on this route · Trips in October 2026 · Home
Asheville 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: Ken Jacobsen / Pexels, Pexels License
- Photo: Ken Jacobsen / Pexels, Pexels License
- Photo: Mark Stebnicki / Pexels, Pexels License




