Three-Oh in Chicago

“I’m gonna tell you somethin’ that you all should know, Chicago is the best place I ever know…” – Jimmy Rodgers

I’ve written about Chicago before, but I love this city so much it deserves as second [and better] post!

Since I was joining “the 30 club” this year, I knew I could pretty easily talk some friends into doing a trip with me if I kept it state-side. I’m proud to say that my plan worked! This was my fifth or sixth time in the city, so it was fun to show a few around who hadn’t been before or at least to some of the places I’ve been to that I love.

We spent four days in this lovely town, and they were four days well spent! Let the birthday activities commence!

Where to stay:

Fieldhouse Jones – It’s like a mix between a hostel and a boutique hotel. Maybe you’d call it an American-style hostel? I say that because they offer private rooms with private bathrooms [which is my kind of hostel!] so it’s not like the traditional ones in other places of the world where you rent a bed in a room with a bunch of random people.

It’s new and in a great location. You’re in the River North area, but it’s a little off the beaten path so you’re not right in the middle of everything. Yet, you still are as it’s only 2 blocks from a train station and a 10 minute walk to Hancock Tower or anything South towards the river.

Cambria – I’ve stayed at this hotel on a previous trip, and if your looking for something that’s in the middle of the madness, then this is your spot! It’s a half block from Michigan Ave. and has a great rooftop for grabbing a pre-dinner drink.

Where to eat:

[Really, this list should be “where not to eat” because there’s more good than bad food in this city…]

Portillo’s – Want a hotdog? Want an Italian beef sandwich? This is your spot. It’ll be crowded, but it’s lightening fast!

Mahalo – It’s in Wicker Park, but worth the short trek there from downtown. I will say that the food overall won’t blow your mind, but you can get a good, fresh poké bowl with their delicious pork fried rice [alright, that was hella good], drink out of a pineapple, and take some good Instagram-able pictures while you’re there.

Hubbard Inn – I would highly recommend the bacon wrapped dates stuffed with goat cheese. Everything else we had was good, but those were GOOD. It’s also in a great location for wandering around for drinks afterwards.

Gino’s East – because, deep dish.

Bridge House Tavern – it’s on the river so you’ll have great views if it’s a nice day! The food was good [we went for brunch], and they have specials every day. Sundays are $5 Bloody Marys and mimosas.

What to do:

Go to the bean – because it’s just fun to go and take pictures.

Go on an architecture tour – On a boat of course. After many visits I finally did one and it was the best touristy thing I’ve ever done. Money well spent!

Go to Wrigleyville – If the Cubs aren’t in town, it’s still a lively neighborhood with your pick of bars and restaurants.

Where to drink:

Hancock Tower – Get sunset drinks at The Signature Room on the 97th Floor – Skip the line at the Sear’s/Willis Tower and go here instead. You’ll pay $17 for a drink, but the views are incredible.

The Violet Hour – A speakeasy in cool, hipster-ish Wicker Park. Need I say more?

Three Dots and a Dash – Another speakeasy, but a tiki bar! Or as I like to call it… a Tiki-sy [cue laughter… but more likely groans].

Henry’s/The Rec Room – Really, the Rec Room is THE SPOT to go, but Henry’s is a good place to hang out before you can head down to the basement bar due to a wait list [eye roll]. It’s also completely worth the wait! It’s a great spot to dance without having to go to a club – if that’s the vibe you’re looking for. We went here two nights in a row because it was so fun!

Underground Wonderbar – Awesome jazz spot. There will be a cover, but totally worth it.

**sadly, it’s now closed! :(**

Big Star – A taste of the South in the Midwest. Live music, BBQ, and good beer. This should be a bar on your list, Southern or not!

Honestly, there are so many good places to go in Chicago where you can’t really go wrong. Wander around Hubbard Street [and probably wait in a line], but you’ll find somewhere fun to stumble into for a while.

Plan for good times! And those jeans to be a bit snug when you leave…


One thought on “Three-Oh in Chicago

  1. I have been to Chicago 3 times (all family trips) and didn’t experience all that you did on you birthday. So glad that you did it right with your girlfriends. Great blog and photos. Thanks for taking the time to share with us! Hope you visit us soon!


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