Chicago from Jacksonville, Oct 30–Nov 1: $1,290 for two, all in
The verdict
Our verdict
Worth it, if
- $103 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.
Round-trip flights on MX + B6 from Jacksonville to Chicago cost $368 per person for Oct 30–Nov 1, 2026 when we checked, $103 below the typical fare on this route. Three places to stay start at $229 a night for the 2-night stay. The total, before you go: $1,214 for two, flights and Hilton Chicago with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$1,290 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $736 |
| Hilton Chicago, 2 nights, two guests, taxes in | $478 |
| Resort fee, collected at the desk | $76 |
| The total, before you go | $1,290 |
| A checked bag each, round trip (not in the total) | about $160 |
$103 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $40 each way per bag on Breeze, $160 for two round trip); 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
$368 per person, round trip
$736 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 | $368 | 1 stop | 32h 51m |
| Frontier | $415 | 1 stop | 26h 48m |
| Frontier | $438 | 1 stop | 25h 37m |
Prices checked Oct 16, 2026, 1:29 AM EDT. 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, Oct 30–Nov 1
Typical highs 51–56°F, lows near 41°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri, Oct 30 | 56 °F | 46 °F | Overcast |
| Sat, Oct 31 | 54 °F | 40 °F | Overcast |
| Sun, Nov 1 | 51 °F | 37 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Chicago
Hilton Chicago
$478 for 2 nights, two guests · $239 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$561 for 2 nights, two guests · $281 a night
See roomsBest Western Chicago Downtown-River North
$458 for 2 nights, two guests · $229 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 | $736 |
| Hotel, 2 nights (Hilton Chicago) | $478 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,734 |
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 | $368 per person |
| Lowest in the last 30 days | $368 (Oct 16, 2026) |
| Typical price, last 60 days | $471 |
| Price checks | 9 |
Good to know
- Passport: no passport needed for travelers 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 $1,734 for two: $736 in flights, $478 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 30–Nov 1?
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 travelers 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 $368 a good price for Jacksonville to Chicago?
It is 22% below the typical $471 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
Nov 14–21, 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
$2,774 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights $955 + hotel $1,595 + resort fee $224, taxes in · a checked bag each adds about $240
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
Oct 30–Nov 1, 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
$764 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $599 + hotel $148 + resort fee $17, taxes in · a checked bag each adds about $200
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.
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Just found · from JacksonvilleWorth it, if
New York City
Oct 23–25, 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
$1,935 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $836 + hotel $968 + resort fee $131, taxes in · a checked bag each adds about $180
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
Oct 23–25, 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
$1,367 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $912 + hotel $394 + resort fee $61, taxes in · a checked bag each adds about $240
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
Oct 30–Nov 1, 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
$871 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $555 + hotel $284 + resort fee $32, taxes in · a checked bag each adds about $160
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
Nov 14–23, 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
$3,562 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights $2,435 + hotel $1,033 + resort fee $94, taxes in · a checked bag each adds about $180
$235 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
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License