Chicago: definitely my kind of town.

Welcome to the land of deep-dish pizza and architectural awesomeness. Where towering skyscrapers meet beautiful beaches, and big city lights energize Midwestern landscapes. Chicago Illinois, a city rich in history and culinary diversity, offers travelers a variety of dining, drink and destination options that are sure to satisfy any appetite.

When faced with so many options in such a large city, knowing where to go (and what you’re expected to find) is half the battle. Fortunately local insight coupled with lots of research led us to some amazing cocktail and culinary discoveries. Here are my top places to check out in Chicago:

DRINK:

Untitled Supper Club – 111 West Kinzie, Chicago IL.

One of my favorite bars in Chicago is a speakeasy style lounge called “Untitled.” The aptly named unmarked and subterranean venue is tucked away next to a parking garage, and difficult to find unless you know what you’re looking for. You will be transported to the 1920’s as soon as you descend the stairs to enter the dimly lit 3-room 17,000 square foot lounge. Everything from the décor and ambiance to the servers and bartenders contribute to the prohibition-era supper club experience. Patrons can enjoy live music and shows (regular burlesque shows) in the main room, or relax with small plates and craft cocktails in one of the 2 side rooms. My favorite aspect of Untitled is the whiskey library featuring over 400 whiskey options.

Terrace at the Trump – 401 N. Wabash, Chicago IL.

An outdoor oasis boasting views of the east side of Chicago, Terrace at the Trump is a great place to grab a cocktail and take in the scenic skyscraper surroundings. Perched atop the 16^th floor of the Trump Tower, you’ll definitely want to include Terrace at the Trump among your Chicago roof top bar stops. The food menu offers everything from small plates to a $100 ice cream Sunday. The drinks are a bit pricy, but you’re really paying for the view – which, again, is spectacular.

Pops For Champagne – 601 N. State St, Chicago IL.

As the name suggests, Pops for Champagne is a cute champagne bar in downtown Chicago. It boasts an impressive Champagne list, cocktails and small plates in a swanky but comfortable atmosphere surrounded by floor to ceiling windows. The menu gives a good amount of background on the champagnes and the servers/bartenders are very knowledgeable and happy to answer any questions. Being a champagne lover, stumbling upon this place while out shopping made my evening, and I would highly recommend it to anyone else who enjoys a good glass of bubbly.

TIP: Below Pops for Champagne is Watershed Bar, an equally cool speakeasy style cocktail lounge that’s also worth exploring.

Signature Lounge – John Hancock Center, 875 N Michigan Ave

Located on the 95^th floor of the John Hancock building, The Signature Lounge offers breathtaking 360 degree views of the city. While the Signature Room (the restaurant on the same floor) requires a reservation, the lounge is open to anyone who would like to grab a drink and take in the spectacular city scene. The cocktails are a little expensive, but you’re really paying for the view.

TIP: There is generally a line/wait to get a table in the Signature Lounge. However, if you tip the host, they will walk you past the line and hook you up with a prime table by the window (you didn’t hear that from me).

DINE:

Quartino – 626 N State St, Chicago IL.

I love Italian food and – fortunately for me and fellow carb cravers – Chicago does it well. Quartino is an Italian restaurant and wine bar, where authentic Italian cuisine meets vintage décor. Small plates are served in a lively and bustling atmosphere. The perennially busy restaurant attests to the quality of its cuisine. However, beyond the amazing food, what stood out to me was the spectacular service. Our waiter was extremely helpful and attentive, and the manager even came to our table to say “hello.”

Lou Malnati’s – Multiple locations

No trip to Chicago is complete without indulging in traditional Chicago-style, deep dish pizza. If you want the best deep dish pizza in Chicago (or, in my opinion, in the country), you have to visit Lou Malnati’s. Lou Malnati’s is pizza perfection. Flakey butter crust, fresh mozzarella, exclusive sausage blend, vine ripened plum tomatoes…my mouth is watering just thinking about it.

Wildberry Pancakes & Café – 130 E Randolph St. Chicago, IL.

Wildberry Pancakes & Café is known for their amazing breakfast food. There is generally a wait for breakfast, but the food is well worth the wait. Menu items are fairly basic, but each contain a unique and delicious twist that make them memorable and delicious.

Giordano’s – 130 E. Randolph St. Chicago, IL

Because I love pizza (especially deep dish), I ate a ton of it while in Chicago. Giordano’s pizza is deep dish deliciousness, and has long been battling Lou Malnati’s for the title of “best deep dish pizza in Chicago.” I recommend trying both and deciding for yourself whose cuisine reigns supreme.

DO:

The Field Museum: 1400 S. Lakeshore Dr. Chicago, IL.

Say hello to “Sue” the largest and most complete Tyrannosaurus Rex ever found. I also loved the Mammoth and Mummy exhibits.

Wendella Architectural Boat Tour: 400 N. Michigan Ave. Chicago, IL.

The Architectural boat tour wasn’t on my initial Chicago “to-do” list. But after being recommended to me by numerous people, I decided to give it a try. I absolutely loved the tour and would recommend it to anyone visiting the city. The guides are very informative and the views from the Chicago river are beautiful.

Millennium Park: 201 E. Randolph St. Chicago, IL.

Take a selfie in the bean (with the rest of the tourists).

Soldier Field: 1410 Museum Campus Dr. Chicago, IL.

Chicago LOVES their football. If you’re going to be in town during the season I highly recommend attending a Chicago Bears game at historic Soldier Field (I’ve been to two now). The energy level and excitement sitting amongst 60,000+ cheering fans is a blast.

TIP: Ladies, leave your purse at home. You need a clear / see-through purse to enter the game.

Navy Pier: 600 E. Grand Ave. Chicago, IL.

It’s a long walk to the end of the pier, but the city views are worth it.

DON’T FORGET:

While you’re busy enjoying Chicago, keep in mind that you’re sharing the city with 2.8 million people, so it’s important to be aware of your surroundings. In Portland, I always walk around with my purse unzipped. However, walking with an open purse in a city like Chicago can make you a target for pick pocketers.