Chicago from Jacksonville, Oct 23–25: round trip from $471
Round-trip flights from Jacksonville to Chicago are $471 per person ($942 for two) from Friday, Oct 23 to Sunday, Oct 25, 2026, for 2 nights on Frontier with one stop. Expect highs of 55–71°F and a small chance of rain. The best-value hotel, Hilton Chicago in the Loop, is $522 for both nights.
The flight
$471 per person, round trip
$942 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 | $471 | 1 stop | 12h 7m |
| American | $591 | nonstop | 2h 53m |
| MX + B6 | $499 | 1 stop | 32h 15m |
Prices checked Oct 12, 2026, 8:14 PM EDT. 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 | $942 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,464 |
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Why go now
$471 per person, all-in, is $8 under the $479 median of the 6 earlier checks we ran on this route, about 2% lower. That's a small edge, not a markdown, and the lowest fare we saw in the last 30 days was $409, so this isn't the floor. What it does get you is a 2-night city weekend for $1,984 for two: $942 in flights, $522 at the Hilton Chicago and $520 of spending money at $130 per person per day. Late October falls between the summer beach season and the holiday markets, which makes this a museums-and-dinners kind of weekend. Friday is 71°F with drizzle, then it's overcast at 60°F on Saturday and 55°F on Sunday. These prices are what we found when we checked, and they can move.
The kind of trip this is
This is a city getaway built around food, architecture and art, with a night of live music if you want one. It suits a couple or two friends who like to walk a lot, eat well and duck into a museum when the clouds roll in. You land at 10:39 PM on Friday, so Saturday is your one full day and the pace is brisk without being rushed.
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 at $522 for the 2 nights ($261 a night) for a King Room, room only, with a 7.9 review score from 981 reviews. Hampton Inn Chicago McCormick Place in the South Loop is the top-rated option, scoring 8.5 from 735 reviews. It's $548 for the stay ($274 a night) and the only one of the three with breakfast included. Hyatt Place Chicago/Downtown - The Loop costs the most at $602 ($301 a night) and has the longest track record, 8.2 across 1,965 reviews. The Hilton and the Hyatt Place are both in The Loop, which puts the architecture, the theatres and Millennium Park right outside your door. Heads-up: none of the three offers free cancellation.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsHampton Inn Chicago McCormick Place
$548 for 2 nights, two guests · $274 a night
See roomsHyatt Place Chicago/Downtown - The Loop
$602 for 2 nights, two guests · $301 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 and see the skyline from the water.
- See the Bean and the fountains in Millennium Park, a short walk from the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, and save it for Saturday night.
- Spend the overcast part of the weekend inside the Art Institute of Chicago.
- Hear live blues at Kingston Mines after dinner.
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 | $942 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,984 |
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 | $471 per person |
| Lowest in the last 30 days | $409 (Oct 13, 2026) |
| Typical price, last 60 days | $479 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- You don't need a passport for this domestic trip, and you'll pay in US dollars.
- Chicago is 1 hour behind Jacksonville, and the 10:39 PM arrival is in Chicago time.
- The Frontier fare leaves JAX at 11:32 AM with one stop and takes 12h 7m to reach O'Hare.
- Prices are all-in, with taxes and fees included, as we found them. They can change before you book.
- You can't cancel any of the three hotels for free, so be sure of your dates before you pay.
Questions readers ask
How much is the flight?
It's $471 per person round trip on Frontier, or $942 for two, all-in when we checked. American has a nonstop for $591 per person that leaves at 6:36 AM and lands at 8:29 AM, 2h 53m in the air, if you'd rather have all of Friday in Chicago.
Do I need a passport?
No. You're flying from JAX to Chicago O'Hare, so it's a domestic trip, and you'll pay in US dollars.
What is the weather like?
Friday is 71°F with drizzle and a 29% chance of rain. Saturday is overcast at 60°F, and Sunday is overcast at 55°F with a low of 48°F. Bring a jacket and an umbrella.
Is 2 nights enough?
It's enough for a first visit if you plan it. The Frontier flight lands at 10:39 PM on Friday, so Saturday is your full day: the river cruise, Millennium Park, the Art Institute and deep-dish. If you want Friday too, take the nonstop.
What does the whole weekend cost?
We estimate $1,984 for two. That's $942 in flights, $522 at Hilton Chicago and $520 in spending money at $130 per person per day.
Which airport do I fly into?
The fares we found land at Chicago O'Hare International (ORD). The city's other airport is Chicago Midway International (MDW).
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License