3 Day Long Weekend Trip to Chicagoland
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
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
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.
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