Worth it from Milwaukee this week, from £443
Milwaukee, WI flies out of Milwaukee Mitchell International (MKE). This week's picks start at £443 per person, return, taxes and fees included. Over the last 30 days the cheapest routes we priced from Milwaukee were Miami (from £240), New Orleans (from £243), New York City (from £248).
11 new picks from Milwaukee this week · last one 5 hours ago · next check in 01:24 · New picks from Milwaukee land here as we find them.
Our picks from Milwaukee right now
Each with the reasons, the catch and the total before you go.
Just found · from Milwaukee
Las Vegas
16 – 18 Oct 2026 · 2 nights
- Nonstop on Southwest, 3h 50m
- Free cancellation at Excalibur
- Highs 79–82°F, little rain expected
£1,973 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,633 + hotel £340, taxes in · a checked bag each adds about £106
Southwest · nonstop · 3h 50m
The catch: £23 per person above the typical fare on this route.
Worth it if you want late nights and a crowd; skip it if you want to sleep.
Tweak this trip
The weekend after · from Milwaukee21% below typicalWorth it, if
Orlando
23 – 25 Oct 2026 · 2 nights
- 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
£1,309 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,104 + hotel £205, taxes in · a checked bag each adds about £121
American. Operated by SkyWest Airlines as American Eagle · with a stop · 19h 42m
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.
Tweak this trip
A week away · from MilwaukeeWorth it, if
Honolulu & Oahu
14 – 21 Nov 2026 · 7 nights
- $588 per person, $243 below the highest fare we saw
- Ramada Plaza by Wyndham Waikiki scores 8 from 1,298 reviews
- Highs of 81–82°F, plus humpback whales offshore in November
£1,688 for two · 7 nights · flights, hotel, taxes & fees
Flights £886 + hotel £802, taxes in · a checked bag each adds about £121
American. Operated by SkyWest Airlines as American Eagle · with a stop · 11h 38m
The catch: With one stop, the flight out takes 11h 38m, none of the three hotels offers free cancellation, and a checked bag runs about $160 for two.
Worth it if a long travel day is fine for a week of warm water and Waikiki; skip it if you need a nonstop or a refundable room.
Tweak this trip
Most loved from Milwaukee
What readers clicked, hearted and shared in the last 7 days.
Just found · from MilwaukeeLowest in 30 days
Miami
27 Nov – 1 Dec 2026 · 4 nights
- Nonstop on American, 7:00 AM out of Milwaukee, 3h 20m to Miami
- $319 per person, $153 below the typical fare on this route
- Normal highs of 78–80°F across all 4 nights
£1,060 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights £481 + hotel £516 + resort fee £63, taxes in · a checked bag each adds about £121
American. Operated by Envoy Air as American Eagle · nonstop · 3h 20m
The catch: A checked bag is about $160 for two and not in the total, and Casablanca Residences Miami Beach has no free cancellation.
Worth it if you want warm beach days, Art Deco streets and Cuban food; skip it if you need clear blue skies every day.
Just found · from MilwaukeeLowest in 30 daysWorth it, if
New York City
5 – 9 Nov 2026 · 4 nights
- $329 per person, $564 below the typical fare on this route
- Westgate New York Grand Central: 8.4 from 1,751 reviews, free cancellation
- Typical highs of 57–64°F for Nov 5–9, good walking weather
£1,648 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights £496 + hotel £1,013 + resort fee £139, taxes in · a checked bag each adds about £106
Southwest · with a stop · 6h 10m
The catch: The Southwest fare leaves at 5:30 AM with one stop, 6h 10m in all, and a checked bag is about $140 for two, not in the total.
Worth it if you'll take an early one-stop flight for this fare; skip it if you'd rather fly the United nonstop at $678 for two.
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Asheville
23 – 25 Oct 2026 · 2 nights
- $664 per person, $604 below the typical fare on this route
- Peak fall foliage on the Blue Ridge Parkway for your dates
- Overcast, highs of 67–77°F, rain chance 8% to 16%
£501 per person · round trip · taxes & fees
Delta · with a stop · 4h 4m
The catch: The lowest fare has one stop and lands at 11:55 PM Friday, and peak foliage brings the busiest weekends of the year.
Worth it if a late Friday arrival is fine for a foliage weekend; skip it if you want a nonstop or quiet trails.
Also priced this week from Milwaukee
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| Miami | 27 Nov – 1 Dec 2026 | £240 | yes |
| New Orleans | 27 Nov – 1 Dec 2026 | £243 | no |
| New York City | 27 Nov – 1 Dec 2026 | £248 | yes |
| Los Angeles | 14 – 21 Nov 2026 | £274 | no |
| Phoenix & Scottsdale | 27 Nov – 1 Dec 2026 | £328 | no |
| Sedona | 27 Nov – 1 Dec 2026 | £328 | no |
| Asheville | 23 – 25 Oct 2026 | £501 | no |
| Cancún | 27 Nov – 1 Dec 2026 | £537 | no |
| Washington, D.C. | 23 – 25 Oct 2026 | £571 | no |
| Nashville | 23 – 25 Oct 2026 | £595 | no |
| Key West | 27 Nov – 1 Dec 2026 | £595 | no |
| Cozumel | 5 – 9 Nov 2026 | £634 | no |
Cheapest routes from Milwaukee, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Miami | £240 | £356 | 6 · nonstop seen |
| New Orleans | £243 | £718 | 14 |
| New York City | £248 | £709 | 14 · nonstop seen |
| Los Angeles | £274 | £371 | 3 |
| Phoenix & Scottsdale | £328 | £379 | 6 |
| Sedona | £328 | £379 | 5 |
| Orlando | £368 | £707 | 8 |
| Honolulu & Oahu | £443 | £616 | 3 |
| Asheville | £501 | £956 | 8 |
| Cancún | £537 | £630 | 6 |
| Washington, D.C. | £571 | £571 | 1 |
| Nashville | £595 | £826 | 6 |
| Key West | £595 | £595 | 1 |
| Cozumel | £634 | £696 | 3 |
| Mexico City | £667 | £667 | 2 |
More trips from Milwaukee
Every other trip page from Milwaukee still ahead of its date.
- Miami, 27 Nov – 1 Dec 2026 from £240 Just found
- New York City, 5 – 9 Nov 2026 from £248 Just found
- Asheville, 23 – 25 Oct 2026 from £501 Just found
- New Orleans, 13 – 17 Nov 2026 from £245 Just found
- Nashville, 23 – 25 Oct 2026 from £595 Just found
- New Orleans, 19 – 23 Nov 2026 from £243 Just found
- Big Island (Kona & Hilo), 14 – 21 Nov 2026 from £717 Just found
- New York City, 16 – 18 Oct 2026 from £429 Just found
Questions about flying from Milwaukee
Which airports do the trips from Milwaukee use?
Milwaukee Mitchell International (MKE). Fares are the cheapest return we found across them for the exact dates, per person, taxes and fees included.
How often do the Milwaukee picks change?
Around the clock: we check live prices every few minutes across the cities and new picks from Milwaukee land on this page as they are published. A pick stays until its departure date, then moves to the archive with the price it had.
What are the cheapest places to fly from Milwaukee right now?
In the last 30 days: Miami from £240, New Orleans from £243, New York City from £248, Los Angeles from £274, Phoenix & Scottsdale from £328, per person return.
Can I ask for a specific trip?
Yes. Use the Ask box: say the destination or the kind of trip and the dates, and a page with live prices appears under Milwaukee within a few minutes.
Planning something from Milwaukee?
Tell us what the trip is for and we pick the one that’s worth it.
Prices converted from US dollars at the rate of 15 Oct 2026.