Chicago from Jacksonville, 30 Oct – 1 Nov: £974 for two, all in
The verdict
Our verdict
Worth it, if
- £78 per person below the typical fare on this route
- Lowest in 30 days on this route
- Typical highs 51–56°F, lows near 41°F this time of year
The catch: Not nonstop: a stop on the way, 32h 51m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Chicago is 2 nights from Jacksonville, 30 Oct – 1 Nov 2026. The cheapest round trip we found is £278 per person (MX + B6, 1 stop, 32h 51m), 22% below the typical £356 on this route. Hotels start at £173 a night; Typical highs 51–56°F, lows near 41°F this time of year.
The total, before you go
£974 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £556 |
| Hilton Chicago, 2 nights, two guests, taxes in | £361 |
| Resort fee, collected at the desk | £57 |
| The total, before you go | £974 |
| Hold luggage each, return (not in the total) | about £121 |
£78 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on Breeze, £121 for two return); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£278 per person, return
£556 for two, taxes and fees included · MX + B6 · 1 stop · 32h 51m
Out Fri, Oct 30, 3:56 PM – Fri, Oct 30, 11:57 PM · back Sun, Nov 1, 7:55 AM – Mon, Nov 2, 8:45 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| MX + B6 | £278 | 1 stop | 32h 51m |
| Frontier | £313 | 1 stop | 26h 48m |
| Frontier | £331 | 1 stop | 25h 37m |
Prices checked 16 Oct 2026, 01:29 GMT-4. 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
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Why Chicago
Why we picked it: Chicago is the best value we priced for the weekend: $368 round trip, 22% under the typical price.
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Weather in Chicago, 30 Oct – 1 Nov
Typical highs 51–56°F, lows near 41°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri 30 Oct | 56 °F | 46 °F | Overcast |
| Sat 31 Oct | 54 °F | 40 °F | Overcast |
| Sun 1 Nov | 51 °F | 37 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Chicago
Hilton Chicago
£361 for 2 nights, two guests · £180 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£424 for 2 nights, two guests · £212 a night
See roomsBest Western Chicago Downtown-River North
£346 for 2 nights, two guests · £173 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
Signature experiences
- 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
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
- Hear live blues at Kingston Mines
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 Jacksonville | Jacksonville International (JAX) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 32h 51m (1 stop) |
| Distance | 864 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £556 |
| Hotel, 2 nights (Hilton Chicago) | £361 |
| Food, getting around and tickets, 2 days for two | £393 |
| Total for two | £1,309 |
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 | £278 per person |
| Lowest in the last 30 days | £278 (16 Oct 2026) |
| Typical price, last 60 days | £356 |
| Price checks | 9 |
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).
Questions readers ask
How much does 2 nights in Chicago from Jacksonville cost?
About £1,309 for two: £556 in flights, £361 for the hotel and £393 for food, getting around and tickets.
What is the weather like in Chicago 30 Oct – 1 Nov?
Typical highs 51–56°F, lows near 41°F this time of year
Do I need a passport for Chicago?
No. No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
How long is the flight from Jacksonville to Chicago?
32h 51m with 1 stop on MX + B6, on the fare we found.
Is £278 a good price for Jacksonville to Chicago?
It is 22% below the typical £356 per person we see on this route, which is why it made the list.
Also found for you
The newest finds from Jacksonville.
Just found · from JacksonvilleLowest in 30 daysWorth it, if
San Francisco
14 – 21 Nov 2026 · 7 nights
- $478 per person, $21 under the $499 typical fare
- Chelsea Inn rated 8.2 from 1,883 reviews, free cancellation
- Marina District base near the Golden Gate and Crissy Field
£2,094 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £721 + hotel £1,204 + resort fee £169, taxes in · a checked bag each adds about £181
Frontier · with a stop · 35h 45m
The catch: The $478 fare has 2 stops and takes 35h 45m on the way out, landing at 11:17 AM the next day.
Worth it if you'd trade one long travel day for a week of city walks and food; skip it if you need a short, easy flight.
Tweak this trip
Just found · from Jacksonville30% below typicalWorth it, if
Destin & the Emerald Coast
30 Oct – 1 Nov 2026 · 2 nights
- $300 per person, $132 below the typical fare on this route
- Village Inn Destin: 8.1 from 1,144 reviews, free cancellation
- Typical highs of 71–72°F, with one clear day on Saturday
£577 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £452 + hotel £112 + resort fee £13, taxes in · a checked bag each adds about £151
Allegiant · with a stop · 30h 30m
The catch: There's 1 stop each way and the return lands Monday, Nov 2 at 5:28 PM, and a checked bag is about $200 for two.
Worth it if you can take Monday off and want a mild beach weekend for less; skip it if you need to be home Sunday night.
Tweak this trip
Just found · from JacksonvilleWorth it, if
New York City
23 – 25 Oct 2026 · 2 nights
- The Cloud One New York-Downtown, part of the Motel One Group, rated 8.8 by 7,961 guests
- Highs 59–69°F, little rain expected
- No passport needed
£1,461 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £631 + hotel £731 + resort fee £99, taxes in · a checked bag each adds about £136
JetBlue · with a stop · 6h 4m
The catch: Not nonstop: a stop on the way, 6h 4m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Tweak this trip
More trips
Next weekend · from JacksonvilleWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- Frontier fare of $456 per person, $16 under the typical $472
- Highs of 77–78°F, with a 6% rain chance at most
- Breakfast and free cancellation at the 7.9-rated best-value hotel
£1,032 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £688 + hotel £297 + resort fee £46, taxes in · a checked bag each adds about £181
Frontier · with a stop · 5h 36m
The catch: The Frontier flight has one stop and takes 5h 36m, and a checked bag is about $240 for two, not in the total.
Worth it if a stop is fine for a $456 fare and live music is the plan; skip it if you want a hotel within walking distance of Broadway.
The weekend after · from Jacksonville19% below typicalWorth it, if
Great Smoky Mountains
30 Oct – 1 Nov 2026 · 2 nights
- Fare is $278 per person, $68 below the typical fare on this route
- Zoders Inn and Suites in Gatlinburg, rated 8.2 from 1,814 reviews
- Typical highs of 60–65°F for Cades Cove and Laurel Falls
£658 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £419 + hotel £214 + resort fee £24, taxes in · a checked bag each adds about £121
MX + G4 · with a stop · 19h 31m
The catch: The outbound has one stop and takes 19h 31m, landing Saturday at 10:05 AM, and a checked bag is about $160 for two.
Worth it if you can sleep through an overnight connection for a fall hiking weekend; skip it if you want a short flight or dry trails.
Nine nights away · from JacksonvilleLowest in 30 daysWorth it, if
Tokyo
14 – 23 Nov 2026 · 9 nights
- $235 per person under the typical fare, lowest in 30 days
- Urban Hotel Morisita scores 8.1 from 269 reviews, free cancellation
- Highs of 57–65°F, and autumn colour in the gardens starts late November
£2,689 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights £1,838 + hotel £780 + resort fee £71, taxes in · a checked bag each adds about £136
£177 per person below the typical fare on this route
B6 + NH · with a stop · 55h 51m
The catch: There are two stops and 55h 51m of total travel time, and checked bags run about $180 for two, which isn't in the total.
Worth it if two long travel days are fine for nine nights of food and city; skip it if you need a nonstop.
All trips from Jacksonville · 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 16 Oct 2026.
Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License