Discover Chicago: A Travel Guide

Ben and I arrived back in Chicago last week after making our way through Laos, Thailand and Cambodia after Christmas. Jet lag is currently killing us, but we’re excited to start working on some posts to share with you over the coming weeks. In the meantime, check out the latest post in our Discover series!

In the “Discover” series, we’ll be offering quick travel tips on things to do, what to eat and where to stay in cities throughout the world! If you’re interested in contributing to the series, send us an email at Enjoy!

Discover Chicago

It’s hard to believe that it’s been five years since I graduated college, packed my belongings and moved to the Windy City! Chicago was a bit of a change from small town Indiana, but I’ve certainly grown to love it. With so many unique neighborhoods, restaurants, shops and activities, there is so much to explore and discover!

Before we dive in, did you know that there are two theories as to why Chicago is referred to as the “Windy City”? The first theory, and most widely accepted, attributes the nickname to the gusty winds that come off Lake Michigan. The second theory dates back to the nineteenth century and refers to Chicago’s long-winded politicians. During that time promoters touted Chicago as a great place to invest, and then later as the best place to hold the 1893 World’s  Columbian Exposition. Which do you believe?

Discover Chicago

Do & Explore

Chicago has a plethora of incredible museums and attractions. Be sure to check out the Art Institute of Chicago and Museum of Science and Industry. The Chicago Architecture Foundation River Cruise is also a touristy activity worth doing. Here are a few more of my favorite things:

Adler After Dark @ Adler Planetarium (1300 S. Lake Shore Drive) – While you can visit Adler Planetarium during normal museum hours, I love their Adler After Dark event. It’s held once a month on Thursday evenings for ages 21+. There’s a different theme for each event, and a $20 ticket gets you access to the exhibits, shows and more. Alcoholic beverages are available for purchase to sip on as you explore.

Adler After Dark

Chicago Riverwalk – The new riverwalk along the Chicago River opened last year and offers a fun place to take an evening stroll. Stop at City Winery for a glass of wine while you watch the boats pass by.

Four Sided (2958 N. Clark St. & 2939 N. Broadway St.) – If you happen to find yourself in Lakeview, stop by Foursided. This is my go-to spot for fun, unique gifts and cute greeting cards.

A New Leaf (1818 N. Wells St.) – Head to Old Town to check out this beautiful flower shop. They make gorgeous flower arrangements and have all sorts of pretty candles, vases, plants and trinkets. There are lots of bars and restaurants further south on Wells Street. It’s also close to Second City if you plan to catch a comedy show.

A New Leaf

Eat & Drink

There are so many amazing restaurants in Chicago! I’d recommend checking out almost anything along Randolph Street in the West Loop, or check out some of my favorite stops:

Beatrix (519 N. Clark St.) – If you’re looking for a good brunch close to downtown, check out Beatrix. They’re relatively new and have two locations that offer a healthy-(ish) menu. They also serve lunch and dinner.

Bar Siena (823 W. Randolph St.) – Bar Siena opened about a year ago in Chicago’s West Loop, offering casual Italian. The restaurant is two stories with some outdoor seating as well. Get a few plates to share with a friend. I love their pizzas, and the Bread and Ricotta appetizer is amazing!

Bar Siena

Cafe Ba-Ba-Reeba (2024 N. Halsted St.) – There are so many restaurants in Chicago that I very rarely go to the same one very many times. But, since moving to Chicago, Cafe Ba-Ba-Reeba has been a favorite that I go back to time and time again. They serve Spanish tapas with delicious, fruity sangria to go along. My favorite dishes include the bacon-wrapped dates, goat cheese baked in tomato sauce and the rioja-raised short rib.

True Food Kitchen (1 W Erie St.) – New to Chicago, True Food Kitchen serves up delicious, healthy meals. We haven’t been able to try it yet (they just opened in November!), but I’m dying to make to it there soon!

Sparrow (12 West Elm Street) – A small 1930’s era bar, Sparrow is a great place to grab a cocktail with a date before or after dinner. I wouldn’t recommend it for a large group.


Kingston Mines (2548 N. Halsted St.) – Located in Lincoln Park, this is a great sport for live blues music. The venue is split into two rooms with a bar and stage in each.  At least two bands will play each night, with one playing on a stage at a time. You can rotate between rooms to be able to view both (you can hear them in either room), or stay put and take a break in between.  Expect to pay a small entrance fee.

Relax & Sleep

To be central to the action, I’d recommend staying within the Loop or River North neighborhoods. They are a ton of options. Keep in mind the price of overnight parking if needed when you’re selecting a hotel – it can be very expensive! Spot Hero is a great app to find cheaper parking options in the city.

Virgin Hotels (203 N. Wabash Ave.) – Recently opened, Virgin is a modern hotel in downtown Chicago. I haven’t stayed here, but it’s in a good location and has rave reviews. There’s a rooftop bar/nightclub and rumor has it that mini bar snack prices are exactly the same as the mini mart around the corner. Rates start at $250/night.

Virgin Hotels

One Thing Not To Do

Don’t forget a bathing suit! If you’re visiting during the summer it’s so fun to check out the beach! There aren’t many places where you can have a beautiful lake in front of you and the city skyline behind you. For a beach close to downtown, check out Oak Street Beach.

Have you been to Chicago? What would you add to this list?

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