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Chicago Midway (MDW) → San Diego

San Diego trip from Chicago Midway (MDW): what 4 nights cost

For 2 travelers, a 4-night San Diego trip from Chicago Midway (MDW) runs about $1,930 to $2,666 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 tripAlaska non-stopManchester Grand Hyatt · 4★$670$1,040$696$260$2,666
Best valueSpirit via Las Vegas (budget fare)Gaslamp hostel, private room · 2★$430$400$696$404$1,930
Least cashSouthwest non-stopGaslamp hostel, private room · 2★$620$400$696$404$2,120

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

  • Coronado Beach dayfree

Day 2

  • La Jolla Cove seals and kayak$100 for 2

Day 3

  • Pacific Beach surf lesson$160 for 2
  • Hodad's burgersOrder: Bacon cheeseburger · in your food budget

Day 4

  • Sunset Cliffs walkfree

Flights from Chicago Midway (MDW)

Round trip for 2.

AirlineStopsTime each wayPrice
Spirit via Las Vegas1 stop6h 29m$430
United Basic Economy via Denver1 stop6h 26m$540
Delta Basic Economy via Los Angeles1 stop6h 39m$570
American via Phoenix1 stop6h 25m$620
Southwest non-stopnon-stop4h 08m$620
United via Denver1 stop6h 26m$660
Alaska non-stopnon-stop4h 08m$670

Food: about $87 a person a day

Breakfast$15
Lunch$20
Dinner$42
Snacks and coffee$10

Restaurants worth the trip

Questions

How much is a 4-night trip to San Diego from Chicago Midway (MDW)?

About $1,930 to $2,666 for 2 travelers, including the round-trip flight, 4 nights of hotel, food and things to do.

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

Spirit via Las Vegas at about $430 round trip for 2.

How much should I budget for food in San Diego?

About $87 a person a day at mid-range places, or $696 for 2 over 4 days.

More from Chicago Midway (MDW)

San Diego costs from every airport

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