Orlando from Milwaukee, 23 – 25 Oct: £1,309 for two, all in
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The verdict
Our verdict
Worth it, if
- Fare is $206 per person below the typical on this route
- Westgate Town Center Resort: 8.5 from 1,755 reviews, free cancellation
- October brings the EPCOT Food & Wine Festival and Halloween events
The catch: The $732 fare has 1 stop and 19h 42m of travel, landing Saturday at 4:01 PM, and a checked bag is about $160 for two.
Worth it if a Saturday evening and a full Sunday in the parks is enough; skip it if you'd rather pay $740 per person for the Southwest nonstop.
Worth it if you can live with a long connection: $1,736 for two is the flights at $1,464 plus 2 nights at Westgate Town Center Resort at $272, taxes and fees included, with checked bags, resort fees and spending money not in it. The trip runs Oct 23–25, 2026, on American Eagle (operated by SkyWest Airlines) with 1 stop and 19h 42m of travel out, landing Saturday at 4:01 PM. Southwest flies the route nonstop in 2h 45m for $740 per person.
The total, before you go
£1,309 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £1,104 |
| Westgate Town Center Resort, 2 nights, two guests, taxes in | £205 |
| The total, before you go | £1,309 |
| Hold luggage each, return (not in the total) | about £121 |
£155 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 American, £121 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
£552 per person, return
£1,104 for two, taxes and fees included · American. Operated by SkyWest Airlines as American Eagle · 1 stop · 19h 42m
Out Fri, Oct 23, 7:19 PM – Sat, Oct 24, 4:01 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American. Operated by SkyWest Airlines as American Eagle | £552 | 1 stop | 19h 42m |
| Southwest | £558 | nonstop | 2h 45m |
| Southwest | £558 | nonstop | 2h 50m |
Prices checked 12 Oct 2026, 14:09 GMT-5. Prices change; the binding price is the one on the booking site.
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Why now
At $732 per person, the fare is $206 below the typical fare on this route ($938), a 22% gap based on 8 earlier checks. Fares we saw for these dates ran from $732 to $944. October is a good month for Orlando because the EPCOT Food & Wine Festival and the Halloween events are both on. The forecast calls for highs of 84°F to 90°F, with rain chances between 17% and 30%. Here's the heads-up: the lowest fare leaves Friday at 7:19 PM and lands Saturday at 4:01 PM, so your weekend is really Saturday evening and Sunday. If that works for you, the whole trip for two is $1,736 with Westgate Town Center Resort, before bags and spending money. If it doesn't, Southwest nonstops at $740 per person get you in on Friday evening.
The kind of trip this is
This is a theme-park weekend for two: one big park day, an evening of festival food at EPCOT and a bit of outlet shopping if you have time left. It suits couples or friends who'd rather do rides, food booths and Halloween events than sit on a quiet beach. The pace is quick, with short nights and lots of walking in 84°F to 90°F heat.
Weather in Orlando, 23 – 25 Oct
Highs 84–90°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 84 °F | 69 °F | 24% |
| Sat 24 Oct | 88 °F | 72 °F | 30% |
| Sun 25 Oct | 90 °F | 72 °F | 17% |
Where to stay in Orlando
Westgate Town Center Resort is our best-value pick. It costs $272 for the 2 nights ($136 a night) for a Deluxe Studio Villa, scores 8.5 from 1,755 reviews and has free cancellation. Vacation Village Orlando, Celebration is the 4-star option at $288 for the stay ($144 a night), also rated 8.5, from 6,950 reviews. Both are in Celebration and both are room only. Holiday Inn Express Orlando - South Park by IHG is the top rated of the three at 9.4 from 239 reviews. It costs $411 for the stay ($206 a night) and includes breakfast. All three offer free cancellation. If you'd rather stay closer to the parks, Walt Disney World Resort hotels come with early park entry and free transport. Lake Buena Vista has lower rates a short shuttle ride from Disney.
Westgate Town Center Resort
£205 for 2 nights, two guests · £103 a night
See roomsHoliday Inn Express Orlando - South Park by IHG
£310 for 2 nights, two guests · £155 a night
See roomsVacation Village Orlando, Celebration
£217 for 2 nights, two guests · £109 a night
See roomsAll hotels in Orlando for these dates
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Where in Orlando
- Walt Disney World Resort: On-site hotels with early park entry and free transport.
- Lake Buena Vista: Hotels a short shuttle from Disney with lower rates.
- Universal Orlando area: Walkable to Universal Studios, Islands of Adventure and Epic Universe.
- International Drive: Central strip with outlet malls, restaurants and attractions.
- Kissimmee: Vacation villas with private pools for larger families.
What to do in Orlando
- Spend Sunday at EPCOT's World Showcase while the Food & Wine Festival is running
- Watch the fireworks over Cinderella Castle at Magic Kingdom
- Ride Hagrid's Magical Creatures Motorbike Adventure at Universal
- Explore the Epic Universe park if Universal is your one park day
- Take a kayak or airboat tour on the Wekiva River for a break from the parks
Also worth it
- Spend a day at EPCOT's World Showcase
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Getting there and around
| Airports in Milwaukee | Milwaukee Mitchell International (MKE) |
|---|---|
| Airports in Orlando | Orlando International (MCO), Orlando Sanford International (SFB) |
| Flight time | 19h 42m (1 stop) |
| Distance | 1,072 miles each way |
| Time difference | +1 hour |
What 2 nights in Orlando costs
| Estimate | |
|---|---|
| Flights for two | £1,104 |
| Hotel, 2 nights (Westgate Town Center Resort) | £205 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,701 |
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: Milwaukee to Orlando
| Per person | |
|---|---|
| This trip | £552 per person |
| Lowest in the last 30 days | £368 (12 Oct 2026) |
| Typical price, last 60 days | £707 |
| Price checks | 8 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Orlando.
- Currency: US dollar (USD).
- EPCOT Food & Wine Festival and Halloween events
- No passport needed, and you'll pay in US dollars.
- Orlando is 1 hour ahead of Milwaukee, and the trip covers 1,072 miles from MKE to MCO.
- The $1,464 fare for two has 1 stop and takes 19h 42m outbound.
- A checked bag is about $160 for two and isn't in the total; we'd plan on about $520 for two in spending money.
- All three hotels offer free cancellation, and only Holiday Inn Express Orlando - South Park by IHG includes breakfast.
Questions readers ask
Is it worth it?
It's worth it for you if the connection doesn't bother you. The fare is $206 per person below typical, but the flight lands Saturday at 4:01 PM after 19h 42m. If you want Friday night in Orlando, the Southwest nonstop at $740 per person takes 2h 45m.
How much is the whole trip for two?
It's $1,736 for two, all in: $1,464 for the flights and $272 for 2 nights at Westgate Town Center Resort, taxes and fees included. Checked bags (about $160 for two), any resort fees and spending money aren't in that total.
Do I need a passport?
No. It's a domestic trip from Milwaukee Mitchell International (MKE) to Orlando International (MCO), and you'll pay in US dollars.
What is the weather like?
The forecast shows Friday at 84°F with a 24% chance of drizzle and Saturday overcast at 88°F with a 30% rain chance. Sunday looks mostly clear at 90°F, with a 17% chance. Lows run from 69°F to 72°F.
Is 2 nights enough?
It's enough for one full park day. With the $732 fare you land Saturday at 4:01 PM, so plan on one evening plus Sunday. Pick EPCOT for Food & Wine or Universal for Epic Universe.
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Prices converted from US dollars at the rate of 15 Oct 2026.
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