How To Plan Your First Trip To Chicago
I finally made it to the foodie capital of America! It’s hard to believe it took me this long to get there, somewhere I have been dying to experience for so long, but I made it. At last, I experienced Chicago! It will not be the last, I am already planning my next visit to this incredible city. First, I wanted to share some Chicago staples and favorites from the locals that will make your first trip as memorable as mine. I will chat with you about choosing your area to stay, places to grub, and the many options of things to do. Now take out your pen and paper, or get ready to screenshot, because you will want to take notes. Unless...you are fine with settling for a mediocre trip, then just save yourself some time and stop reading all the special tips that are coming your way. Those who are with me, let’s get going!
Home Sweet Home
There seems to be some great little neighborhoods to stay in Chicago. I’m sure the more often you visit, the more fun it would be to venture around trying new spots, different hotels or even an AirBnB. After speaking with a few locals and Chicago natives, if it’s your first time visiting the city, it is best to stay in River North.
River North - Although you could find cheaper lodging in other areas, River North or somewhere close by is a great option for first timers because it is the most urban area with many bars and restaurants.
No Time To Get Hangry
Like I said, “Foodie capital of America.” Chicago is home to so many appreciable gems like their famous deep dish pizza and Chicago style hotdogs. Besides the local favorites, this city has many michelin star restaurants as well. So, if that’s your thing, go knock yourself out, you will not be disappointed with the various options. Regardless, there are endless amounts of possibilities for top-notch, quality food just about anywhere you stumble into.
If your don’t get the classic deep dish pizza, just remember to still get the butter crust with the deep dish you create!
First-Timer Musts:
Lou Malnati’s - for deep dish (Giordanos is the other major chain) I went to Lou’s, loved it! Everyone says that’s the better one to go to :) Get the deep dish cookie for dessert too! Try to go before/after lunch and dinner rush or else you’ll have a two hour wait! They don’t take resos. In any case, it’s worth the wait!
RPM Italian - Come here for a nice Italian dinner, the best Italian you’ll find in the city! Owned by celebrities Giuliana and Bill Rancic. We tried an assortment of pastas and apps. Every bite was outstanding.
Portillo’s - Chicago style hotdogs, plus so much more! Neat, casual place, a true Chicago staple. I made the rookie mistake of eating my Chicago hotdog wrong. Jot down this important information so you don’t f*@k up as well...the pickle goes ON the hotdog!
Do you see my pickle on the side? Yeah, don’t do that…it goes ON the hotdog and gets eaten WITH the hotdog. #rookiemistake
Locals Love:
Girls and the Goat (if can’t get a reso go to Little Goat)
Au Cheval
Tanta - Peruvian
Beatnik - nice waterfront views
Etta
Siena Tavern
Friends Sushi - great sushi, small place
Pierrot Gourmet - casual, amazing “chocolate obsession cake”
Nico
Mon Ami Gabi (Lincoln Park)
Feeling Fancy:
Lawry’s Steakhouse
Alinea
Maple and Ash
Snacks and Fun:
Nutella Cafe - If you love Nutella and you don’t go here, do you really even love Nutella? If you purchase a personalized Nutella jar, remember to check it in your luggage or security won’t let you through with it in your carry on.
Eataly - Italian market with lots to eat and shop around
Their spread of donuts and coffee is endless, so many deliciously, unique options.
Stan’s Donuts - Great donuts and coffee!
Garrett Popcorn - True Chicago staple! Purchase a bin to take home, they will seal it for you and you can take it passed security at the airport no problem!
Sprinkles - If you haven’t heard of these delicious cupcakes, then let me just tell you…here in Chicago, Sprinkles Cupcakes has an ATM machine. That’s right, you just walk up to the machine, pick out your cupcake, swipe your card, and then the magic happens! POOF! Your cupcake appears. Not only this is awesome, they are the best cupcakes you’ll ever eat!
Quench Your Thirst
Along with all the delicious food options, come fun spots to either stop in for a beer or make a night of some good old bar hopping. I found a wide variety from casual breweries to fancy cocktail bars and everything in between. Depending on whether you prefer day drinking, the nightlife party, or casual sips of wine, you are guaranteed to find your sweet spot.
The Goose Island Brewery has an amazing everything pretzel, it comes with unreal bacon jam and a mouth watering cheese dip.
Getting Tipsy:
Breweries: Goose Island and Revolution are the big ones. Goose island has great food.
Chicago Athletic Club Hotel is across the street from Millenium Park. It has a fun bar/game room/rooftop called Cindy’s.
Sweetwater - lots of beer options if beer is your thing, good casual spot
Pinky Out Cause You Fancy:
The Aviary - make reservations for a cocktail tasting
The Signature Lounge at 96th
Drunkenly Hip:
Moneygun - Speakeasy hidden in a restaurant
Three Dots and a Dash - Speakeasy tiki bar
The Drifter - Speakeasy, enter Green Door Tavern, walk through the bar, head down the stairs in the back, and you’ll come to a waiting room. Might be a wait.
The Milk Room - Speakeasy on the second floor of Chicago Athletic Club Hotel
Watershed - Speakeasy, head into Pops for Champagne and find the stairs in the Southeast corner of the bar
Lone Wolf - Vintage style cocktail bar across the street from Girl & The Goat
Parlor Pizza - Pizza & lively bar with big outdoor patio
Federales - Popular taco spot with big beer garden
Waydown - rooftop bar
For more rooftop bars visit: http://www.chicagorooftopbars.com/terrace-at-trump.html
SO Much Room For Activities
Wait, there’s more to do in Chicago besides eat and drink? During the summer there’s a long list of sightseeing landmarks, museums, markets, concerts, and many other attractions to keep you busy. Slip on your comfy shoes and let’s go!
If you don’t take a picture at the Bean, did going to Chicago even happen?
Bean There, Done That:
Millennium Park has the famous landmark, Cloud Gate, better known as the Bean (oval metal reflective statue).
Millennium Park offers a variety of movies, concerts and workout sessions. Check link for days and times: https://www.chicago.gov/city/en/depts/dca/supp_info/mp_calendar.html
View of the city from the top deck of our boat tour. Pack a rain coat or umbrella to be safe!
Chicago boat architecture tour. Great way to see the city and on some tours they have a bar :) This was a fantastic tour! Highly recommended!
Segway tours looked fun as well, however, didn’t do one of these.
Skydeck at Willis Tower or John Hancock Tower are a fun way to see the city. The Skydeck, at the top of the Willis Tower, has a great view and you can take a picture on The Ledge (glass box overlooking the city). Lines can be long, but save a couple hours for this attraction, they move quickly. Purchase tickets online to help save some time.
Navy Pier (Pier with the Ferris wheel) is a Chicago staple, worth seeing, but it can be crowded and food/drinks will be super expensive. It is a nice walk down the pier and to the beer garden at the end. Definitely check it out!
Lincoln Park Zoo is worth a quick trip if you have time. It’s free and you can go through quickly.
Chicago Cubs Baseball Game - The atmosphere in Wrigleyville is electric! If you are a sports fan, a baseball fan, or just like a good time, you MUST plan your trip during a Cubs’ home game. Take the train up to Wrigleyville and get there a couple hours before the game starts to take a picture in front of the famous Wrigley Stadium without a large crowd, but more importantly, to go to the bars to pre-drink with all the fans! We went to a bar and grill called Cubby’s. It was right across the street from the stadium. It had great drinks, got packed with Cubs fans and also had great food! The bleacher seats are usually the cheapest, and that’s where the party is at for sure! On a hot day you’ll want to be in the shade, that’s something hard to predict, so go with your comfort. Regardless, it will be a packed stadium with loyal, merry fans who know how to host a good baseball game and a better time!
Magnificent Mile - The main road that makes a great walk. It is loaded with tons of shopping, so if shopping is your thing, start here. There are many pockets of upscale clothing and jewelry stores as well in the River North area.
My kind of shopping however, is still revolved around food if you can’t notice.
Food Tours - I didn’t sign up for one, but I did hear from many individuals that Chicago has some great food tours to offer with options like local cuisine to exploring Chinatown. Book ahead of time, space is limited!
Pretty Cool If You’re Into Them:
Art Institute of Chicago
MCA (Museum of Contemporary Art) They do a small farmers market outside every Tuesday. https://www.mcachicago.org/Programs
Field Museum
Shed Aquarium
That’s A Wrap (and not the kind you eat)
So that is all I have, but just for now! I will definitely be traveling back to Chicago to revisit some of my favorite spots and to explore much more! Like the tour guide on our boat tour said, “Chicago is always changing, so visitors always have new things to come back to.” I can’t wait to see what my new friend, Chicago, has planned for me next time.
Encore:
Everything in Chicago is very accessible by the L (loop train) or Uber
Lyft was cheaper than Uber
Midway Airport is closer to downtown
Make reservations for dinner spots
You can take a water taxi to the museums
Go in the summer to get the best weather