Saturday, June 6, 2015

Operation Friend VACA - Chicago

One of the hardest things about moving to the East Coast from SF 7 years ago was leaving my best friend Diana. We had worked together at Riordan HS: an all boys school, which presented us with a daily laugh track. Other than my college best friend Sasha, who I lost to cancer this year, I never knew two girls could be so close. Diana is my sister, and I miss her everyday. With Sasha gone, I understand more than ever the urgency of making time to see each other - especially since anyone who knows me will tell you that I avoid the phone like the plague. Thus, "Operation Friend VACA" is in effect.

Mission: plan a 4/5 day getaway for my best friend Diana and I to reconnect in July

Challenge: cost (we are both teachers) and distance (I live in NYC, Di lives in SF)

Our Previous Trips: Nicaragua, Vegas, Key West, Santa Fe

Possibilities: Puerto Rico, Austin TX, Savannah GA, Chicago IL... After some preliminary checking, I found the most cost effective from both SFO and JFK is Chicago:


Inbound Tues  July 7
SFO - ORD American Airlines Red Eye: arrive in Chicago 5:59 am AA1522
LGA -  ORD American Airlines arrive in Chicago 8:37 am AA307

Outbound Fri July 10
ORD - SFO Virgin  6:40 pm VX 0211
ORD - LGA American Airlines 6:35 pm AA348

Hotels - 4 star

Wyndham Grand Chicago Riverfront $255
Hotel Chicago Autograph Collection $223
Westin Michigan Ave $183
Millennium Knickerbocker $167
Fairmont Millennium $189 special rate (winner!)

Planned Itinerary (all prices for 2 tickets)

Wrigley Field
Stubhub $241
We both love baseball so Wrigley Field is a no brainier : 7:05 pm Wed 7/8 night game against Cardinals - Upper Deck Infield Box 429 Row 1
Best Seats at Wrigley

Architecture Foundation River Cruise
Ticketmaster $102
10 am Reservations on Thurs - arrive 9:30

Hop on and Off Tour
Groupon $64
48 hours hop on and off

16 Best Affordable US Vacations
Fodor US Trip Picks
Trip Advisor: 3 days in Chicago
Top 25 Things to Do Time Out
Must Eat: Deep Dish Pizza
Millennium Park: Chicago Bean
Water Tour Plaza on Magnificent Mile
360 Chicago
Taste of Chicago Festival
Viator Top Ten Tours

I'm impressed with the people from Chicago. Hollywood is hype, New York is talk, Chicago is work. - Michael Douglas

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