3 Day Long Weekend Trip to Chicagoland

by | Nov 14, 2013

1st Day 

  • 8:33 am: Flight from SFO to Chicago
  • 2:48 pm: Arrive in O’Hare International Airport
    • Took the local bus to get downtown
  • 4:30 pm: Check into the Sheraton Hotel & Towers
  • 5:30 pm: Happy hour at Devon Seafood Grill
    • Snacked on cocktails and bar snacks
  • 7:00 pm: Head to Trader Joe’s
    • Picked up some snacks and drinks
  • 7:30 pm: Go back to hotel
    • drink and relax before our diner reservation
  • 9:00 pm: Walked over to the restaurant
    • Turned out to be a 45 minute odd walk in the cold night
  • 9:45 pm: Reservation at Girl & The Goat
    • An amazing multiple course birthday dinner for our friend

Close Up of Frank's Chicago Dog

Day 2 

  • 8:00 am: John went to Corner Bakery to pick up breakfast for us
  • 9:30 am: Wake up and get ready for a day of exploring Chicago
  • 10:00 am: Take the local metro bus to Hot Doug’s
  • 11:30 am: Eat at Hot Doug’s for Lunch
    • 3 foie gras dogs
    • 1 Chicago dog
    • Duck fat fries
  • 1:30 pm: Go to BadHappy Poutine
    • The Good, The Bad and the Happy poutine made with truffle mayo and foie gravy
  • 3:00 pm: Head back to hotel to rest and pack
  • 4:00 pm: Check out of Sheraton and taxi to the Langham Hotel
  • 5:00 pm: Enjoy amenities of Langham since it was raining
    • Jacuzzi
    • Pool
    • Steam rooms
  • 8:30 pm: Dinner at Epic
    • Seared foie gras
    • Black cod
    • Tiger prawns
  • 10:30 pm: Head back to hotel and rest

Girl and the Goat's Fried Egg on Top of Pork Cheek on a Fancy Sauced Plate

Day 3

  • 7:30 am: Get up and watch the start of the Chicago Marathon
    • Oddly we seem to have a history of going places that have marathons
  • 8:00 am: Breakfast at Travelle inside the hotel
    • Lobster benedict with truffle hollandaise
    • Lobster and spinach
  • 9:30 am: Visit Millennium Park
    • This is where the big shiny “bean” is located
  • 10:20 am: Visit Navy Pier
    • Walked around
    • This would have been really cool at night during warmer weather
  • 11:00 am: Head back to Langham
    • More jacuzzi
    • More pool
    • Some more spa again
  • 1:15 pm: Check out of the Langham
    • Leave our luggage with the front desk
  • 1:35 pm: Lunch at Lou Malnati’s For deep dish pizza
    • The Lou Malnati’s original deep dish pizza
    • Malnati’s salad was recommended for the salad dressing
      • It was good!
  • 2:45 pm: Go back to Langham to pick up luggage
  • 3:15 pm: Take bus and then train to airport
  • 5:25 pm: Leave O’Hare International Airport
  • 8:07 pm: Land back at San Francisco Airport

Price Breakdown | $350 Per Person

United Round Trip Flight to Chicago from San Jose for both of us came to about $440 USD.

The entire stay, after points, in Chicago came down to about $350 USD for the 2 of us minus airfare.

You and another could do our entire trip for less than $780 USD plus food and drink.



What do you like to eat while in Chicago?

You're going to eat, you might as well eat something tasty.
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