Featured Gluten-Freedom Lifestyle Travel

Chicago Weekend Guide

January 20, 2020

I was recently asked by my mom to help her recommend some fun things to do in Chicago over the long weekend. Her friends were looking for some trendy neighborhoods to stay in, good restaurant recommendations, as well as some interesting Chicago activities for cold weather. I love this kind of stuff, and I take pride in knowing all the must-go places to check out in Chi city – so after I rattled off the world’s longest email to my mother I thought, why not do the same here on the blog for all of my Life’s A Beacham friends?

So without future ado, here is my Chicago weekend guide: perfect for three day weekends, romantic getaways, overnight business trips and more! All of the restaurants I’ve recommended are places to safely dine #glutenfree unless stated otherwise.

Where to Stay:

  1.  Hyatt Centric Mag Mile  (Downtown) There are a ton of fun boutique hotels to stay at in Chicago – but if you want to stay on Mag Mile I’d recommend the Hyatt Centric Chicago Mag Mile – it’s right off of Michigan Avenue, a hop and a skip away from my favorite GF (and regular) donuts, Do-Rite Donuts on Erie and close to the lake so you can walk to the lakefront path. There’s also a Lyfe Kitchen a block away for a healthy quick lunch. 
  2. The Godfrey Hotel (Gold Coast) If you’re into staying away from the Mag Mile, but still want to be close to the lake, look into the Godfrey hotel in Gold Coast (walking distance to Division street bars, Wells Street food, and Viagra Triangle)
  3. Hotel Lincoln (Old Town/Lincoln Park) For something less fancy but conveniently located in Old Town by Second City and all the restaurants on Wells Street – Hotel Lincoln. Their roof top is to die for.
  4. The Robey (Wicker Park) I’ve also heard wonderful things about The Robey in Wicker Park. Right in the heart of all of the foodie fun. Checkout their rooftop for epic skyscraper views, Big Star down the street for tacos and see if you can get into the The Violet Hour – the speakeasy kitty-corner, for a Twin Peaks behind the curtain vibe. 

Fun Things to do Day and Night:

  1. Book tickets to the interactive art exhibit put on by the Art Institute – https://thegameshowgameshow.com
  2. See a Blackhawks game at the United Center – https://www.unitedcenter.com/events-and-tickets/
  3. Go to Second City, or iO theatre for a show –  https://www.secondcity.com/shows/chicago/  https://www.ioimprov.com/tickets/
  4. It’s probably too chilly to do the architecture tour but you can always hop on a water taxi for the experience – https://www.chicagowatertaxi.com
  5. Go to Ballast Point brewery in West Loop and try all the beers (not GF) – https://www.ballastpoint.com/location/chicago/
  6. Go to the Chicago History Museum on North & Clark – https://www.chicagohistory.org/visit/

Fun Bars:

  1. The Drifter is a speakeasy in the basement of the Green Door Tavern (head to the basement and knock on the right hand side at the bottom of the stairs, there will be a wait to get in on a weekend but this is about as cool as it gets when it comes to authentic speakeasies and they have really good live acts) – https://www.thedrifterchicago.com 
  2. Book a reservation at The Darling on Randolph in West Loop (this is another speakeasy) – https://thedarlingchi.com
  3. Cindy’s is always a good bar to go to for views of Millennium Park and a fun vibe. You can book dinner there too – http://www.cindysrooftop.com
  4. The Vig on Wells gets really young late at night on the weekends but their cocktails are awesome and you can walk anywhere on Wells street – I also highly recommend getting the French fries (shameless YouTube plug go check out my vids) – http://www.thevigchicago.com
  5. Bub City is the place to go for live country and a dance floor – http://bub-city.com/chicago/
  6. Kingston Mines is a Chicago landmark for live blues music – https://www.kingstonmines.com
  7. Maudes Liquor Bar in West Loop is about as cozy as it gets for ambiance and cocktails – http://www.maudesliquorbar.com

Chicago-Style Restaurants:

  1. The Weiner circle – Go grab a Chicago-style hot dog, they’re rude to you on purpose so get ready for that (Not GF) – https://www.wienercircle.net
  2. Pequod’s Pizza – Chicago local’s opinion of the best deep dish (Not GF) – https://pequodspizza.com/chicago
  3. Gibsons – the original Chicago steakhouse in Viagra Triangle with killer dirty martinis – https://www.gibsonssteakhouse.com/locations/gibsons-chicago/
  4. DO YOURSELF THE FAVOR – Go get a burger at Small Cheval, either at the Wells street or Wicker Park location http://smallcheval.com

Chicago Cuisine:

  1. Sushi – Tanoshii Sushi Mike’s West Loop Location – http://tanoshiisushi.com 
  2. Italian – Monteverde – http://monteverdechicago.com  & Nico Osteria – https://www.nicoosteria.com 
  3. Steak – Bavettes – http://bavettessteakhouse.com/chicago/  & Swift & Sons – https://www.swiftandsonschicago.com &  Maple & Ash https://www.mapleandash.com
  4. Mediterannean/small plates – Ema – https://www.emachicago.com &  Aba – https://www.abarestaurants.com
  5. Woodfired Pizza – Forno Rosso on Randolph – http://www.fornorossopizzeria.com

Tips for Tourists: 

  • Keep your wallet in your front pocket and your purse zipped! 
  • MAKE RESERVATIONS there’s no such thing as a walk in on a weekend.
  • The homeless really appreciate leftovers. 
  • The L isn’t worth it if you’re sticking close to the Lake. Either embrace the bus or just take an Uber/Lyft. 
  • Pretty much anyone on the street will help you find your way – it’s the Chicago mentality!
  • You will need gloves and a hat.
  • Don’t be afraid to venture out to Lakeview for more food, fun and culture.
  • When in doubt, find the Lake (you’ll then be facing East) and you’ll be able to navigate from there. 

I hope this Chicago Weekend Guide is something you feel you can recommend to friends and family, no matter what age. If there’s anything I absolutely MUST add to the list that’s in these neighborhoods – let me know! I am constantly adding to my own list so I selfishly would love to hear about any new spots in my favorite town. #Lifesabeacham

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