I’m updating this blog post pandemic, which seems insane to say. I’m also dedicating this blog to my two new team members Dee and Shannon, who showed me that instagram now allows little bloggers like me to link to their posts! Thanks ladies, for inspiring me to get back to something I love.
This post is here to help you plan a trip to Chicago. I’ve included some trendy neighborhoods to stay in, restaurant recommendations, as well as some interesting Chicago activities for cold & warm 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 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:
- 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.
- 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, and Viagra Triangle)
- **New for 2022 – The Thompson Hotel (Gold Coast) I really can’t say enough good thing about The Thompson. It’s very well located, in the heart of Gold Coast with shopping and good eats surrounding, but it’s also a Hyatt property so you can use points to book it. Absolutely check out their hotel restaurant Nico Osteria, they’ve unfortunately removed their GF pasta option but they are extremely accommodating with gluten free and the fresh Italian cuisine and cocktails are truly a treat to have right in the hotel.
- 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:
- Book tickets to the interactive art exhibit put on by the Art Institute – https://thegameshowgameshow.com
- See a Blackhawks/Bulls game at the United Center – https://www.unitedcenter.com/events-and-tickets/
- Go to Second City, or iO theatre for a show – https://www.secondcity.com/shows/chicago/ https://www.ioimprov.com/tickets/
- Cheap and cheerful, hop on a water taxi for the experience – https://www.chicagowatertaxi.com
- Even better – take the architecture tour on the river and finally understand why literally everyone raves about it.
- Chicago has about 8 million farmers markets and street festivals happening each weekend, I recommend checking out what’s going on when you’re in town and picking a few to check out. The Old Town and Wells Street Art Fairs are both fantastic walkable options where art food and music combine.
- Go to the Chicago History Museum on North & Clark – https://www.chicagohistory.org/visit/
- Go to a Cubs game 🙂 Wrigley has had a major facelift the past few years and is now a more family friendly area to hang out in, but don’t worry, all the old baseball bars are still open for business!
- 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.
- Book a reservation at The Darling on Randolph in West Loop (this is another speakeasy.
- 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.
- 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)
- Bub City is the place to go for live country and a dance floor.
- Kingston Mines is a Chicago landmark for live blues music.
- Sparrow is a Havana themed bar right under the nose of the Hangee Uppe, and I bet you’ve never noticed it! But you should – it’s a small cozy spot where the bartender will make you anything you like, should one of their many fun cocktails not sound up your alley. This is where Dermot and I had our first date, so I can say it’s a vibe 🙂
- DO YOURSELF THE FAVOR – Go get a burger at Small Cheval, either at the Wells street or Wicker Park location http://smallcheval.com
- Gibsons – the original Chicago steakhouse in Viagra Triangle with killer dirty martinis – https://www.gibsonssteakhouse.com/locations/gibsons-chicago/
- 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
- Pequod’s Pizza – Chicago local’s opinion of the best deep dish (Not GF) – https://pequodspizza.com/chicago–
- Sushi – Tanoshii Sushi Mike’s West Loop Location – http://tanoshiisushi.com
- Italian – Monteverde – http://monteverdechicago.com & Nico Osteria – https://www.nicoosteria.com
- Steak – Bavettes – http://bavettessteakhouse.com/chicago/ & Swift & Sons – https://www.swiftandsonschicago.com & Maple & Ash https://www.mapleandash.com
- Mediterannean/small plates – Ema – https://www.emachicago.com & Aba – https://www.abarestaurants.com
- 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 can get you some places but not all, and in the summer it’s not my favorite mode of transportation. Either embrace the bus, grab a Divvy bike, or 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 unless it is June, July, August or September.
- Don’t be afraid to venture out to other neighborhoods 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