A weekend in Chicago

Stay at 

The Belden Stratford if you’re made of money and are over 40

The Wit if you need all-day access to swanky rooftops

 

Central City:

The Signature Lounge is in the Handcock Building. Go here instead of the observatory because the observatory costs moolah just to look out the window. The Lounge doesn’t cost anything, you’re just expected to buy a drink…booze and amazing views of the city…fine!

If its nice out, walk along the lake to Oak Street Beach. There’s a Beach Bar near the water… booze and lake michigan…fine!
Here are some bars you can google in this area that normally have good specials and good atmosphere: The Kerryman, Cedar Hotel (outdoor patio), Market.
Eat lunch at Xoco, Rick Bayless is god in the mexican food world,
 
Wrigleyville:
Clark street (the road that the field is on) is sports bar after sports bar after sports bar. If there’s a game going on, there will be swarms of drunk idiots stumbling around.
If you’re in that area, you MUST go to Tango Sur. It’ll give anyone an instant boner. It’s BYOB and the food is incredible. You can share one plate because they give you wayyy more argentinian meat than one human should ever consume in one sitting. Bring at least two bottles of wine… you won’t want to leave. There’s almost always a wait but it is sooooo worth it.
 
Wicker Park/Bucktown:
This is like the Williamsburg of Chicago. Piece Pizza is a huge brewpub on North Avenue. Good place to start off a night in this area. Or Big Star, its a hipster taqueria with super cheap food. Then you can literally stumble from door to door for the rest of the night. every bar is weird and different.
 
Randolph Street
The food mecca of the city right now. Eat at Girl and the Goat. There will be a wait. Wait. It’s worth it. FYI – The lounge area to the right of the entrance is first come first serve seating.
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