Tripfitly
Chicago Midway (MDW) → Orlando

Orlando trip from Chicago Midway (MDW): what 5 nights cost

For 2 travelers, a 5-night Orlando trip from Chicago Midway (MDW) runs about $2,224 to $2,494 with the round-trip flight, hotel, food and things to do. Here are three ways to spend it.

Plan it with my dates and budget

Three plans

PlanFlightHotelFlightHotelFoodThings to doTotal
Best tripSouthwest non-stopSpringHill Suites Orlando Theme Parks · 3★$450$800$800$444$2,494
Best valueSpirit non-stop (budget fare)International Drive budget hotel · 2★$350$400$800$744$2,294
Least cashJetBlue non-stopSpringHill Suites Orlando Theme Parks · 3★$460$800$800$164$2,224

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

  • EPCOT$280 for 2

Day 2

  • Gatorland$70 for 2
  • 4 Rivers SmokehouseOrder: Smoked brisket · in your food budget

Day 3

  • ICON Park wheel$60 for 2
  • Hawkers Asian street foodOrder: Roti canai · in your food budget

Day 4

  • Boma African buffetOrder: Zebra domes for dessert · $34 for 2 over your food budget

Day 5

  • East End MarketOrder: Graze the market stalls · in your food budget

Flights from Chicago Midway (MDW)

Round trip for 2.

AirlineStopsTime each wayPrice
Spirit non-stopnon-stop2h 39m$350
Delta Basic Economy via Atlanta1 stop4h 54m$390
United Basic Economy via Washington1 stop5h 35m$390
American via Charlotte1 stop5h 01m$440
Southwest non-stopnon-stop2h 39m$450
JetBlue non-stopnon-stop2h 39m$460
Delta via Atlanta1 stop4h 54m$470

Food: about $80 a person a day

Breakfast$14
Lunch$18
Dinner$38
Snacks and coffee$10

Restaurants worth the trip

Questions

How much is a 5-night trip to Orlando from Chicago Midway (MDW)?

About $2,224 to $2,494 for 2 travelers, including the round-trip flight, 5 nights of hotel, food and things to do.

What's the cheapest flight from Chicago Midway (MDW) to Orlando?

Spirit non-stop at about $350 round trip for 2.

How much should I budget for food in Orlando?

About $80 a person a day at mid-range places, or $800 for 2 over 5 days.

More from Chicago Midway (MDW)

Orlando costs from every airport

Make it yours

Change the dates, budget, travelers and how you eat, or add your points and miles.

Plan my trip