Maui trip from Chicago Midway (MDW): what 6 nights cost
For 2 travelers, a 6-night Maui trip from Chicago Midway (MDW) runs about $4,014 to $5,874 with the round-trip flight, hotel, food and things to do. Here are three ways to spend it.
Plan it with my dates and budgetThree plans
| Plan | Flight | Hotel | Flight | Hotel | Food | Things to do | Total |
|---|---|---|---|---|---|---|---|
| Best trip | Southwest non-stop | Hyatt Regency Maui Resort · 4★ | $1,170 | $2,880 | $1,344 | $480 | $5,874 |
| Best value | Southwest non-stop | Paia surf inn · 2★ | $1,170 | $960 | $1,344 | $540 | $4,014 |
| Least cash | Southwest non-stop | Kihei condo · 3★ | $1,170 | $1,380 | $1,344 | $540 | $4,434 |
Best trip skips budget airlines, Basic Economy and hostels. Best value and Least cash may use them to save money.
The Best trip, day by day
Day 1
- Molokini snorkel cruise$260 for 2
Day 2
- Kaanapali Beach dayfree
Day 3
- Waiʻānapanapa black sand beach$20 for 2
Day 4
- Surf lesson$180 for 2
Day 5
- Iao Valley hike$20 for 2
Day 6
- Hoʻokipa turtles and windsurfersfree
Flights from Chicago Midway (MDW)
Round trip for 2.
| Airline | Stops | Time each way | Price |
|---|---|---|---|
| United Basic Economy via San Francisco | 1 stop | 11h 20m | $1,010 |
| Delta Basic Economy via Salt Lake City | 1 stop | 11h 20m | $1,120 |
| Alaska via San Francisco | 1 stop | 11h 20m | $1,120 |
| Southwest non-stop | non-stop | 9h 06m | $1,170 |
| American via Los Angeles | 1 stop | 11h 26m | $1,230 |
| United via San Francisco | 1 stop | 11h 20m | $1,240 |
| Hawaiian via Honolulu | 1 stop | 11h 40m | $1,260 |
Food: about $112 a person a day
Breakfast$20
Lunch$25
Dinner$55
Snacks and coffee$12
Restaurants worth the trip
- Mama's Fish HouseOrder: Fish caught that morning · about $110 a person
- Leoda's piesOrder: Chocolate haupia cream pie · about $15 a person
- Foodland pokeOrder: Shoyu ahi poke · about $15 a person
- Ululani's shave iceOrder: Shave ice with ice cream underneath · about $8 a person
- Monkeypod KitchenOrder: Mai tai with honey-lilikoi foam · about $45 a person
Questions
How much is a 6-night trip to Maui from Chicago Midway (MDW)?
About $4,014 to $5,874 for 2 travelers, including the round-trip flight, 6 nights of hotel, food and things to do.
What's the cheapest flight from Chicago Midway (MDW) to Maui?
United Basic Economy via San Francisco at about $1,010 round trip for 2.
How much should I budget for food in Maui?
About $112 a person a day at mid-range places, or $1,344 for 2 over 6 days.
More from Chicago Midway (MDW)
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