3 Day Long Weekend Trip to Chicagoland

by | Nov 14, 2013

1st Day 

Close Up of Frank's Chicago Dog

Day 2 

  • 8:00 am: JM head to Corner Bakery to pick up breakfast
  • 9:30 am: Wake up and get ready
  • 10:00 am Take metro/bus to Hot Doug’s
  • 11:30 am: Eat at Hot Doug’s for Lunch
    • (3 foie dogs, 1 Chicago dog and 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/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 and steam rooms)
  • 8:30 pm: Dinner at Epic
    • seared foie, 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
  • 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 “bean” is located
  • 10:20 am: Visit Navy Pier
  • 11:00 am: Head back to Langham
    • jacuzzi/pool/spa again
  • 1:15 pm: Check out of Langham
  • 1:35 pm: Lunch at Lou Malnati’s For deep dish pizza
    • The Lou Malnati’s original pizza and Malnati’s salad
  • 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 Chicago 
  • 8:07 pm: Arrive in SFO

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.
Please Share and Comment!
Something is wrong.
Instagram token error.