CHICAGO
I cannot tell you how many times I have put off writing this Chicago visitors guide. I’m coming to realize it’s been a challenge to start because I don’t want to have to choose my favorite spots. Growing up in close proximity, Chicago reminds me of home. It’s a place I know and love.
Chicago obviously has the big city life, but adds more of a mid-western pace that you don’t get from New York. There are new restaurants and bars popping up all the time so while my favorites do change, there are some that will always stay. I’ve listed both new and old favorite spots, some of the best touristy destinations, where to stay for the first timer and even my favorite place to stay when I visit. If you’re new to the city or have been there for years, I hope you enjoy seeing some of the places that make Chicago great.
WHERE TO STAY IN CHICAGO
BEST AREA FOR FIRST TIMERS
For your first time in Chicago, you’ll want to be in the middle of it all and I recommend staying in the Loop or River North. You’ll be close to shopping, restaurants and some of the best nightlife.
MY FAVORITE HOTEL: HOTEL VICEROY
I’m a bit obsessed with the Viceroy brand. They know how to do hospitality the right way. Plus, it’s located in one of my favorite neighborhoods in the city, Gold Coast. It’s close to great shopping and restaurants without the same congestion that the Mag Mile brings. With a rooftop pool and bar, this spot is equal parts perfect for relaxation and fun.
Some other hotels I recommend:
+ Loews Chicago Hotel
+ The Gwen
+ Pendry Chicago
+ The Langham
CHICAGO BREAKFAST EATS
FOR THE CLASSICS: YOLK
If you’re looking for a classic no-frill breakfast, Yolk is your place. There are plenty of locations around the city so no matter where you’re staying there is one bound to be close.
FOR A HIPSTER MORNING: GODDESS
The Goddess and The Baker is perfect for those who are looking for an avocado toast or grab-n-go pastry. I love to order a coffee and walk right up the street to the river walk and enjoy the view. You can also take a seat inside and order my personal favorite, the yogurt parfait.
FOR A BREAKFAST CLUB VIBE: KANELA
My friend used to live in Chicago and she introduced me to Kanela. The cute breakfast join has a few locations around the city, but if you’re in the Ukrainian village, pop in and order the french toast. You won’t regret it.
FOR A LAVISH BRUNCH: MAPLE & ASH
I don’t think it’s any surprise that I love brunch. There’s something about some champagne with a side of breakfast food that makes me happy. Maple and Ash has found a way to perfect their brunch menu. Ask about their champagne bar cart. You won’t regret it. Plus, look at those cute straws!
CHICAGO LUNCH & DINNER EATS
FOR THE BEST DEEP DISH: LOU MALNATI’S
I mean this isn’t even a debate anymore, right?! Most Chicagoan’s will go to bat for either Giordano’s or Lou Malnati’s, but in my opinion Lou’s wins every time. Pequod’s is a close second for me, though.
FOR THE BEST HOTDOG: PORTILLO’S
This should come as no surprise. Every visitors guide to Chicago says to visit Portillo’s. But, I don’t go to Portillo’s for the hot dogs. I go for their burger and milkshake. Yes, call me crazy. I love their burgers. I like to think it’s their best kept secret, but what do I know? So, while you should go for the hot dogs, come back for the burger!
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FOR BIG GROUPS: QUARTINO
This is always a must when I visit Chicago so it’s a must on this visitors guide to Chicago. Quaritino has some of the best Italian food and the atmosphere is so authentic to Italy. It’s also a great spot for larger groups as they have multiple levels with a menu designed to share. Be sure to get a reservation ahead of time.
FOR A RIVER NORTH GO-TO: HUB51
More often than not when I am hungry and in the River North area, I end up eating at Hub51. It’s a tried and true spot for me. I’ve never had a bad meal here and the food is always consistently good. What more could you ask for?
Great margarita’s and taco’s? Sign me up every time. You order at the counter at this quick Mexican restaurant owned by Rick Bayless. It’s great for lunch or when you just need something to eat before a night on the town.
FOR MEXICAN STREET FOOD: XOCO
Great margarita’s and taco’s? Sign me up every time. You order at the counter at this quick Mexican restaurant owned by Rick Bayless. It’s great for lunch or when you just need something to eat before a night on the town.
FOR A WOOD-FIRED MENU: ETTA
Delicious food and a great atmosphere await at Etta. And, if you visit in the warmer months, their rooftop patio makes the perfect location for lunch.
FOR A GIRLS LUNCH: SUMMERHOUSE SANTA MONICA
Summerhouse Santa Monica is located in Lincoln Park and great for a lunch or brunch with the girls. The decor here is dreamy and the food is made for those who are looking for a light but filling lunch. I love their brussel sprout salad.
FOR AL FRESCO DINING: DAWSON
All I need to say about Dawson is to start with the ceviche appetizer. Their outdoor dining area would win me over on its own, but the food is worth staying for.
FOR A SPECIAL OCCASION: GIRL & THE GOAT
Scoring a coveted reservation at Girl & The Goat should be enough of a reason to celebrate. While getting in is tough, it shouldn’t steer you away from this eatery. Be sure to plan in advance so you can celebrate those special occasions at the chef’s table. And, save room for dessert here!
CHICAGO BARS
FOR A GNO: BEAUTY BAR
A beauty salon by day and 90’s themed bar by night? Yes, please! I love going here with the girls for a night full of dancing.
FOR A TIKI DRINK: NO BONES BEACH CLUB
If you love mezcal or a tiki drink then hit up this gem tucked away in Bucktown. Even if you hate mezcal, still head inside for a summer getaway in the dead of winter.
If you love mezcal or a tiki drink then hit up this gem tucked away in Bucktown. Even if you hate mezcal, still head inside for a summer getaway in the dead of winter.
FOR A NIGHT OF DANCING: DISCO CHICAGO
Complete with a light up dance floor and disco ball, this spot can get anyone up and dancing.
FOR A DIVE BAR: RAINBO CLUB
Coolest part about this bar? Head to the back of the bar for an old school photobooth.
FOR CUBS GAMES: SLUGGERS
I may have a few too many here, but this bar is always a good time for before, during and after a Cubs game.
CHICAGO ROOFTOP BARS
- FOR THE BEST VIEW: london house
- FOR THE BEST PARTY: joy district
- FOR A HIDDEN GEM: celeste
- FOR A PRE-DINNER DRINK: cerise
- FOR POST-DINNER DRINKS: upstairs at the gwen
CHICAGO SWEET EATS
FOR GELATO: EATALY
I am a sucker for good gelato and Eataly always hits the spot. Inside is more than just gelato, though. You can eat, drink and shop your way through Italy while there.
FOR DONUTS: DO-RITE
Whether it’s for a quick morning breakfast or a sweet treat, my favorite donuts in the city are from Do-Rite.
FOR THE BEST ICE CREAM FLAVORS: JENI’S
This Chicago visitors guide would not be complete without mentioning Jeni’s. Some of the best and unique flavors os found here.
WARMER MONTH ACTIVITIES IN CHICAGO
+ MICHIGAN AVE BEACH & RIVERWALK
+ CONCERT AT WRIGLEY OR TINLEY PARK
+ CUBS GAME
+ BOATING ON LAKE MICHIGAN
COLDER MONTH ACTIVITIES IN CHICAGO
+ ICE SKATING IN MILLENIUM PARK
+ CHIRISTKINDLMARKET
+ LIGHTING OF THE TREE
+ CONCERT AT RIVIERA THEATRE
CHICAGO TOURIST ACTIVITIES
+ NAVY PIER
+ SKYDECK CHICAGO
+ ART INSTITUTE OF CHICAGO
+ MAG MILE
+ MILLENIUM PARK & THE BEAN
Chicago has a plethora of activities and dining spots. Don’t agree with something I recommended? Shoot me a note and convince me otherwise. I would love to chat with you about what you love about the city or what you think I should add on my visitors guide to Chicago!
