Chicago

Why Chicago?  The food, architecture and that aqua blue lake
Must See & Do: Bike along the lake; stroll through Lincoln Park and take an architecture boat tour.

Explore

Chicago is a city of neighborhoods, each with it's own personality. Try and tackle them one at time.  Here are a few suggestions:

Downtown/The Loop:  There a lots of tourist attractions here - plenty to fill up a weekend. Here are some suggestions:
  • Millenium Park - Stunning park featuring stunning modern art & archtecture including Anish Kapoor's Cloud Gage (AKA the Bean), Frank Gehry's Pritzker Pavillion and BP Bridget, Jaume Plensa's Crown Fountain and the peaceful Lurie Garden. 
  • Art Institute of Chicago
  • Aquarium & Field Museum 
  • Architectural boat tour - this is fantastic!
  • Michigan Ave for shopping
  • Navy Pier (warning - this is very touristy and usually really crowded)
  • If it's warm enough, rent bikes and ride along the Lake up to Lincoln Park (or if you are ambitious go all the way up to Evanston)

Gold Coast/Old Town/Lincoln Park: Many residents live in these beautiful neighborhoods north of the city along the lake. 
  • Brownstone walking tour: Start by walking up Dearborn street in the Gold Coast. When you reach North Ave go up one block and walk through the heart of Old Town along Wells Street. Then walk up to Arlington Street and head west and explore the beautiful brownstones of Lincoln Park. It's fun to get lost here. 
  • Street Festivals: If you visit in the summer check the street festival schedule. Some favorites include the Sheffield Garden Walk, Air & Water Show and Old Town Art Festival. 
  • Halstead & Arlington is a great spot for boutique shopping and cafes

Lakeview/BoysTown/Wrigleyville
  • This neighborhood holds a special place in our hearts because it's our old stomping grounds. There a lots of great restaurants, bars and shops sprinkled throughout these neighborhoods. 
  • No trip to Chicago is complete without a visit to Wrigley Field. Try and catch a game and definitely enjoy the party scene before and after a game in Wrigleyville. 

Wicker Park/Bucktown
  • Hipster central. Here you can find lots of indie shops, bars and quirky restaurants.  

eat, drink, be merry...snooze

There are a  TON of amazing restaurants in Chicago and new ones keep opening all the time. Here area few suggestions:
  • Steak:  Tango Sur -  Argentine steakhouse on Southport. It's BYOB so pick up a bottle of red and enjoy a great steak! 
  • Sushi:  Japonais  
  • Tapas:  Cafe Baba Reeba in Lincoln Park or Cafe Iberico in the Gold Coast
  • Pizza: Chicago Pizza & Oven grinder in Lincoln Park - they serve upside down pizzas. Also try Piece in Bucktown.
  • Vietnamese: Le Colonial
  • Marathon Meal: Alinea in Lincoln Park. We once ate a 22 course meal here! Book far in advance.
  • Cozy Cafe: Matisse on Diversey
  • Lunch Cafe: Bourgeios Pig in Lincoln Park
  • Brunch: Yolk or Nookies
  • Noodles: Pennys on Diversey
  • Live Music: Kingston Mines (Blues), Green Mill (Jazz), House of Blues Gospel Brunch, Joe's on Weed Street
  • Late Night Bars: Hangge Uppe,  Katacomb, Beaumonts
  • Concerts: The Vic, Northerly Island, Park West, Lincoln Hall

Hotels. If you can splurge, stay at the Trump. If not try and find a deal online anywhere downtown or north. 

Tunes

Impossible Germany - Wilco
Chicago - Sufjan Stevens
This Too Shall Pass - OK Go
Thirty Three - Smashing Pumpkins
She's a Jar - Wilco
Dear Chicago - Ryan Adams
The People - Common
Home -Kanye West
Superstar  - Lupe Fiasco
I Want You to Want Me - Cheap Trick
You're the Inspiration - Chicago
Bad Bad Leroy Brown - Jim Croce
My Kind of Town - Frank Sinatra
Tonight, Tonight - Smashing Pumpkins
Thanks for the Memories - Fall Out Boy