Chicago from Jacksonville, 23 – 25 Oct: £1,104 for two, all in
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The verdict
Our verdict
Worth it, if
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522 for two nights
- Fare of $471 per person, $8 below the $479 median
- Highs of 55–71°F, with rain chances of 29% or less
The catch: The Frontier fare has one stop and takes 12h 7m to get there, and a checked bag is about $240 for two on top.
Worth it if you'll trade a long Friday of travel for the lower fare; skip it if layovers on a 2-night trip wear you out.
Worth it if you can handle a long travel day. The trip is $1,464 for two: the Frontier flights at $942 plus 2 nights at Hilton Chicago at $522, with taxes and fees included, but not a checked bag or spending money. You travel Oct 23–25, 2026, and the fare has one stop, with 12h 7m door to gate on the way out.
The total, before you go
£1,104 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £710 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £1,104 |
| 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
£355 per person, return
£710 for two, taxes and fees included · Frontier · 1 stop · 12h 7m
Out Fri, Oct 23, 11:32 AM – Fri, Oct 23, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £355 | 1 stop | 12h 7m |
| American | £445 | nonstop | 2h 53m |
| MX + B6 | £376 | 1 stop | 32h 15m |
Prices checked 12 Oct 2026, 20:14 GMT-4. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $471 per person, the Frontier fare is $8 below the $479 median of our earlier checks on this route, or 2% under. The lowest we saw in the last 30 days was $409, so this isn't the floor, but it's a fair price. Add Hilton Chicago in The Loop at $522 for two nights and the whole trip comes to $1,464 for two, taxes and fees included. A checked bag and spending money aren't in that number. Late October is a good fit for a city weekend. The forecast shows 71°F on Friday, 60°F on Saturday and 55°F on Sunday. It's mostly overcast, with rain chances between 16% and 29%. That's weather for museums, a river cruise and deep-dish, not the beach. Prices are as we found them when we checked, and they can move.
The kind of trip this is
This is a quick city weekend built around architecture, art, food and live music. It suits a couple or two friends who like to walk a downtown, eat well and stay out for blues. You land at 10:39 PM on Friday, so Saturday is your big day. Keep the pace brisk and centered on The Loop, where most of what you'll want is within walking distance.
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
We'd stay in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. Hilton Chicago is the best value at $522 for the stay ($261 a night) for a King Room. It scores 7.9 from 981 reviews, and it's the hotel counted in the total. Hampton Inn Chicago McCormick Place in the South Loop is the top rated, with 8.5 from 735 reviews. It's $548 for the stay ($274 a night), and it's the only one that includes breakfast. Hyatt Place Chicago/Downtown - The Loop scores 8.2 from 1,965 reviews at $602 for the stay ($301 a night). None of the three offers free cancellation, so be sure of your dates before you book. If nightlife matters most, River North is the city's nightlife core.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsHampton Inn Chicago McCormick Place
£413 for 2 nights, two guests · £207 a night
See roomsHyatt Place Chicago/Downtown - The Loop
£454 for 2 nights, two guests · £227 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
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Saturday afternoon at the Art Institute of Chicago
- 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 Jacksonville | Jacksonville International (JAX) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 12h 7m (1 stop) |
| Distance | 864 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £710 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,495 |
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: Jacksonville to Chicago
| Per person | |
|---|---|
| This trip | £355 per person |
| Lowest in the last 30 days | £308 (13 Oct 2026) |
| Typical price, last 60 days | £361 |
| Price checks | 6 |
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).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Jacksonville.
- The outbound flight leaves JAX at 11:32 AM and lands at O'Hare (ORD) at 10:39 PM after one stop.
- None of the three hotels offers free cancellation.
- A checked bag is about $240 for two and isn't in the $1,464 total.
Questions readers ask
Is it worth it?
Worth it if you don't mind a long travel day. The fare is $8 below the $479 median, and The Loop hotel is rated 7.9. The catch is one stop and 12h 7m on the way out, which is a lot for a 2-night trip.
How much is the whole trip for two?
$1,464 for two, all in, with taxes and fees included. That's the Frontier flights at $942 plus 2 nights at Hilton Chicago at $522. It doesn't cover a checked bag, about $240 for two, or spending money.
Is there a nonstop?
Yes. We found an American nonstop at $591 per person, or $1,182 for two. It leaves at 6:36 AM and lands at 8:29 AM, 2h 53m in the air. That gives you a full Friday in the city.
What is the weather like?
Highs of 71°F on Friday with possible drizzle (29% chance), then 60°F on Saturday and 55°F on Sunday, both overcast. Lows run from 48°F to 57°F, so pack a jacket.
Is 2 nights enough?
For a focused city weekend, yes. With the Frontier fare you land at 10:39 PM Friday, so Saturday is your one full day. Pick the river cruise, the Art Institute, deep-dish and blues.
Do I need a passport?
No. It's a domestic trip, and you'll pay in US dollars. Chicago is 1 hour behind Jacksonville.
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All trips from Jacksonville · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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- Photo: Mik Dominguez / Pexels, Pexels License
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