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Chicago Midway (MDW) → San Francisco

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

For 2 travelers, a 4-night San Francisco trip from Chicago Midway (MDW) runs about $1,838 to $2,698 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-stopGrand Hyatt San Francisco · 4★$700$1,120$832$46$2,698
Best valueSpirit via Las Vegas (budget fare)Fort Mason hostel, private room · 2★$480$480$832$46$1,838
Least cashSouthwest non-stopNob Hill boutique hotel · 3★$640$840$832$46$2,358

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

  • Walk the Golden Gate Bridgefree
  • House of Prime RibOrder: Prime rib, carved at the table · $46 for 2 over your food budget

Day 2

  • Chinatown and North Beach walkfree
  • Tartine BakeryOrder: Morning bun · in your food budget

Day 3

  • Lands End trailfree
  • Swan Oyster DepotOrder: Crab back and Sicilian sashimi · in your food budget

Day 4

  • Ferry Buildingfree
  • La Taqueria burritosOrder: Carnitas burrito, dorado-style · in your food budget

Flights from Chicago Midway (MDW)

Round trip for 2.

AirlineStopsTime each wayPrice
Spirit via Las Vegas1 stop6h 48m$480
Delta Basic Economy via Salt Lake City1 stop6h 38m$570
American via Los Angeles1 stop7h 06m$620
Southwest non-stopnon-stop4h 23m$640
Delta via Salt Lake City1 stop6h 38m$700
Alaska non-stopnon-stop4h 23m$700
United non-stopnon-stop4h 23m$710

Food: about $104 a person a day

Breakfast$18
Lunch$24
Dinner$52
Snacks and coffee$10

Restaurants worth the trip

Questions

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

About $1,838 to $2,698 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 Francisco?

Spirit via Las Vegas at about $480 round trip for 2.

How much should I budget for food in San Francisco?

About $104 a person a day at mid-range places, or $832 for 2 over 4 days.

More from Chicago Midway (MDW)

San Francisco costs from every airport

Make it yours

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

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