Chicago Travel Guide

Dress by Amanda Uprichard

The Windy City is neither as big nor glamorous as New York and it doesn’t have the Hollywood appeal of Los Angeles. Yet millions flock to Chicago every year to admire its original architecture (steel skyscrapers were pioneered here), and to visit its numerous cultural institutions and historical sites. There are over 7,000 restaurants and nearly 2000 bars to visit by night, and on sunny days visitors can take advantage of 26 miles of lakefront , complete with bike paths and bathing beaches.

Chicago is jam-packed with amazing things to see and do- so much that I couldn’t even begin to fit them all into a blog post. With that said, I’ve found some places that I particularly love during my last few trips, so I wanted to compile what I’ve been “loving lately” in the Windy City for those of you who plan to visit soon.


Sky Deck –

Experience the glass balcony extending four feet outside the 103rd floor of Willis Tower 😍

Navy Pier –
While it can get pretty crazy during peak summer hours, Navy Pier is such a fun way to escape the city-vibes. It’s located right on the beach, and even houses some of Chicago’s most iconic restaurants. The brand new ferris wheel is one of the best ways to take in the entire Chicago skyline.

Architecture River Tour –

For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than the water. You’ll spy more than 40 architecturally significant buildings, including the John Hancock Center, the Wrigley Building, the Aon Center and Willis Tower, as you drift along the Chicago River. An expert guide will give you the lowdown on Chicago’s rise from the Great Fire of 1871, the advent of balloon-frame construction and other crucial moments in the city’s history. $43.68

The Magnificent Mile

Outfit Details – Click the image

Officially known as Michigan Avenue, The Mag Mile has everything from Chanel to Forever21. It’s easy to spend an entire day on this one-mile strip as it’s covered in not only stores but restaurants, access to the riverfront, historical buildings, access to the beach, and so much more.

Field Museum-

Get off the couch, gather up the family, and go explore the Field Museum of Natural History in Chicago. One of the many exciting institutions that makes up the city’s museum campus, the Field Museum offers great attractions for everyone. From best preserved Tyrannosaurus Rex fossil to Inside Ancient Egypt, Underground Adventure , mummies from ancient Peru and Egypt and so much more.


Hampton Social –

You’ve probably seen their ‘rose all day’ sign on Instagram, but this is one you definitely have to check out in person. This adorable place evokes East Coast living in every aspect. They have a ‘rosé of the day’ and you HAVE to try the frosé (Tito’s, rosé, and peach purée). Also – Bassment – the bar beneath The Hampton Social – is one of my favorite bars during the summer.

Summer House Santa Monica
It’s no secret that winters in Chicago are well, the majority of the year. Thankfully a little bit of summer exists year-round in the Lincoln Park neighborhood at SummerHouse. The retractable ceiling, greenery, rosé cart, and twinkly lights make you believe, even if just until you look outside, that you’re in Southern California. Aside from the incredible interior, SummerHouse is run by one of Chicago’s most famous restaurant groups and serves a wide variety of options.

Let’s be honest, we’re all guilty of wanting to post that over-the-top treat on Instagram—and BomboBar makes it easy to do so. From their adorable outdoor coffee window to their donut topped hot chocolate, everything they serve not only looks amazing but tastes great too.


Click the image for Outfit Details

The Drake
This iconic hotel is located directly in between the beach and Michigan Avenue, a location that truly can’t be beat. The luxury hotel also houses high-end boutiques. The Palm Court, where you can have afternoon tea, is known for notable guests such as the late Marilyn Monroe and Princess Diana.

Easily one of my favorite spots in the city, DL Loft can be rented out for both events and as a place to stay. The Parisian-inspired loft houses a full kitchen, two bedrooms, a living room, and even a huge private patio.

Chicago Athletic Association
This recently renovated hotel located in Chicago’s loop is just seconds from Millennium Park, home to “The Bean.” While its location is great, the hotel has enough amenities for you to never leave and still enjoy a packed weekend. Take in the incredible views while grabbing drinks at their rooftop restaurant, play some pool in the game room, and snack on a late night burger from Shake Shack, all within the hotel.

The Guesthouse Hotel
If you live in Chicago and are hoping for a little “staycation,” this is your place. Located just north of the city in Andersonville, The Guesthouse Hotel is one of the most stunning spaces this city has to offer.

Hotel Lincoln
This boutique hotel is located within the Lincoln Park neighborhood and overlooks Chicago’s zoo. A new restaurant owned by one of Chicago’s most famous restaurant groups is set to open within the lobby in summer 2017!

Chicago continues to surprise me and stole a little piece of my heart. If you’ve never been, it’s without a doubt somewhere you need to add to your list. I’m so happy I got so spend some time “home away from home” and I can’t wait to come back.


3 thoughts on “Chicago Travel Guide

Leave a Reply