Chicago City Guide. {where to eat, sleep & play.}

 In travel
chicago city guide

Every time I visit Chicago I always ask myself, “why don’t I don’t come here more often?”


For being only 4ish hours away, it’s so easy to escape to the city life for a weekend. Being that we do visit on a semi-regular basis, however, we’ve definitely established our favorites. A weekend getaway with my amazing in-laws is on the books, which has me counting down the days until I’m back in the city. Here it is: where to eat, sleep & play in Chicago!

where to eat…

Y’all already know I’m a foodie… I seriously plan all travel activities around my stomach! From brunch & beverages to dinner & desserts (& more beverages), here are my Windy City Faves:


Little Goat Diner.

820 W. Randolph St., West Loop | 312.888.3455

I’m a sucker for breakfast food & I’m all about that brunch life. First of all, this is Stephanie Izard’s version of an American diner (aka: you may know Stephanie from her stint on Top Chef where she was the first female chef to smoke the competition… #girlboss). Second of all, Little Goat Diner serves breakfast all day. Not your typical “diner breakfast,” either… we’re talking Ooey Gooey Cinnabuns & Bull’s Eye French Toast (read: eggs. crispy chicken. sweet onion brioche. bbq maple syrup).



1112 N. State St., Gold Coast. | 312.586.2150


Truth be told, I haven’t been here. Yet. However, I most definitely did just book a reservation… because, from what I hear, this spot is the bee’s knees. What I’m looking forward to most on their brunch menu: Monkey Bread. I mean, seriously. When a classic is not only on the menu… but the first one listed, you just go with it. Also currently catching my attention: the Competitors Punch (vodka. raspberry. lime. soda water. an entire bottle of cava). #done



Booth One.

1301 N. State Pkwy., Gold Coast | 312.649.0535


This place is special for us: it’s where we celebrated our very first “dateiversary” in 2012, & back then it was the Pump Room. As they like to say, “an iconic restaurant reinvented,” I swoon over this place because of the old-school atmosphere – servers wear tuxedo jackets, there are giant booths, & the light fixtures are just dreamy! While I don’t remember what we each ordered on that first anniversary of the rest of our lives, D. is a sucker for Dover Sole & I’m a sucker for anything lemon, so Ms. Hsing’s Lemon Meringue Napoleon is calling me from the dessert menu.

chicago city guide

Pequod’s Pizza

2207 N. Clybourn Ave., Lincoln Park | 773.327.1512


I am a pizza connoisseur, without a doubt. & yes, Lou Malnati’s has been a go-to for me for years, as has Gino’s East. However… I like to steer clear of chains, when I can, & Pequot’s had me at “caramelized crust.” I mean, I haven’t met a pizza I didn’t fall in love with, but this one definitely has my heart.

where to sleep…

Location, location, location. This is how I select my hotels in Chicago. (Or in any city, really!) But I also want to have great big windows, a view of downtown, room service & an aesthetic worthy of an Instagram post.

Thompson Chicago

21 East Bellevue Place, Gold Coast | 312.266.2100
We stayed at Thompson for good friends’ wedding last fall, & I fell in love with the place. The location was great (as in, a short walk to fabulous shopping), the aesthetic is urban modern meets cozy, & the room had the most amazing robes in it!
chicago city guide
chicago city guide

The Waldorf Astoria

11 E. Walton St., Gold Coast | 312.646.1300
The rooms are spacious, the views are insane, the location couldn’t be better, & the service is impeccable. &, I really am living my best life when I’m getting pampered at the spa.
Chicago City Guide

where to play…

Where to start?! Shopping… check. Sports… check. Theater… check. Museums… check. Music… check. Architecture… check. Water… check. Seriously, I forget how much I really love Chicago!


Michigan Ave.

There’s really too much to list out individually, because this is the mecca… But the one stop I must make every time I’m in town is:


Neiman Marcus | 737 N Michigan Ave. Again, I’m a sucker for the customer experience. Shoes, handbags, apparel, accessories & all designer, all under one roof… I mean, of course. I have a stylist that has become a great friend, & he knows my style oh-so-well. If you’re ever in the store, ask for “Chris Theobald.” (I found Chris while shopping suits for D, but he has become my go-to guy as well. That’s right, I share him with my husband!) Tell him I sent you, & hello!


Oak Street. 

Luxury designer’s row. They’re all here, ladies: Tom Ford, Chanel, Dior, Barneys New York… you name it. It’s heavenly.



Aritzia | 923 N Rush Street. Aritzia has been a fav of mine for… geez… 10+ years! I used to shop the Water Tower Place location, but have since fallen in love with the Chicago flagship on Rush. I fell in love with Aritzia because of the customer experience, which is something they pride themselves on, but I have stayed & gone back (again & again!) because of the clothes. Beautiful. Minimalist. Neutral. Well made, & at a great price point.


Blake | 212 W. Chicago Avenue. I originally learned of Blake thanks to my obsession with Gwenyth Paltrow & learning that this is one of her fave boutiques on the planet… & she’s never steered me wrong, so of course I had to check it out. They stock everything from Rick Owens to The Row to Saint Laurent, & round it out with more mid-priced brands like L’Agence. The buyers have amazing taste; it’s hard not to fall in love with this place.


Intermix | 40 East Delaware Place. A collection of the most sought-after styles from so many great designers. The staff is always great about assisting & love to style you, & if you happen to hit the SALE you’ve struck gold.





Chicago Cubs at Wrigley Field. 

Listen, I hate baseball. Seriously. I find it to be so dull & games are entirely way too long, as is the season. I literally refuse to watch it on tv. However, there is something about seeing the Chicago Cubs play at Wrigley Field that is a pretty memorable life moment. I’ll admit. Cubs fans are kinda the best.

chicago city guide

Chicago’s First Lady Cruises

Probably my favorite thing I’ve ever done in Chicago is the architectural river cruises. Totally worth the time & it will give you a new-found appreciation for such a beautiful city.

Lake Michigan Beaches. 

The ocean of the Midwest. It’s freezing cold… but, it’s a freaking blast of a place to spend a day in the summer.

chicago city guide

Have you been to Chicago? Where are your favorite places to eat, sleep & play?

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