Chicago holds a special place in my heart. Being born and raised in the suburbs of this great city it’s easy to take for granted all the amazing things the Windy City has to offer. I decided to create a guide to some of my favorite places.
Where to Eat & Drink
I may be a little bias but Chicago has some of the best food. Similar to other big cities like LA and NYC, the city offers a wide variety of cuisine from all backgrounds and walks of life. Today I’ll stick to the classics that we are known for.
Without further ado, here are some must try’s while in Chicago.
Classic Deep Dish | Giordianos
One of the first things that comes to mind when thinking of Chicago is our deep dish. For Chicagoans its a never ending debate on whether Giordianos or Lou Malnatis is superior. Personally, I’m a Giordianos girl but you really can’t go wrong with either one.
Italian Beef | Portillos
Portillos hits it out of the park with a lot of their food options from their Italian Beef (extra wet) to their hot dogs and cheese fries. For the salad fans, their chopped salad with house dressing is amazing.
Hot Dogs | Gene & Judes
People drive an hour from the suburbs just to get these hot dogs. Its a sin in Chicago to have ketchup on your hot dog be prepared to for that.
Flaming Saganaki | Greek Islands
It doesn’t get much better than an entire block of cheese for cheese lover when it comes to Saganaki. The flames aspect adds for a fun experience no matter which Greek restaurant you chose.
Rooftop Bars
Nothing beats the vibes of a rooftop bar in the summer especially in Chicago. Here are a few favorites with amazing views.
+LondonHouse
Londonhouse has amazing views of the river that flows through the city. Everything about it is upscale, luxurious and classy. It’s a great place to go with friends.
+Upstairs at the Gwen
You’re surrounded by beautiful skyscrapers at the Gwen. It’s not as busy as some of the other rooftops which makes for a nicer experience. I consider it one of my new favorites.
+Cindy’s Rooftop
Cindy’s is a very popular location right across the street from the Bean and a straight 20 minute walk from the train stations. It can get pretty crowded but the drinks are good and the view can’t be beat.
+Utopian Tailgate
A great colorful atmosphere with great views and fun games awaits a Utopian Tailgate. It has a younger energy to it and is a little further from the hustle and bustle of downtown.
What to Do
There is an endless amount of things to do in the city. Regardless of age, budget and interests there’s definitely something for everyone.
+Museum of Contemporary Art
There is a lot to experience and see at this museum, you can easily spend a few hours here. The pieces are all so unique and interesting.
+Shedd Aquarium
Who wouldn’t want to go see the fishies? The lines may be long but it’s still a great family experience. I loved getting to see ‘Dory’.
+River Cruise
Take things off land, its a great way to see the city from a different perspective. The Chicago architecture is truly beautiful and a river cruise is well worth the money.
+Maggie Daley Park
I love coming here in the winter for the ice skating rink. It’s a great place in the summer as well with multiple playgrounds for kids.
+Navy Pier & the Ferris Wheel
Navy Pier is constantly expanding their restaurants and events to even bigger and better. The ferris wheel is a fun addition to experience the views, going right around sunset is magical.
+Willis Tower
An iconic spot to visit in Chicago. Test your fear of heights by stepping onto the glass ledge that is on the 103rd floor.
+Summer Concerts(Spring Awakening, Lollapalooza, Movies in the Park)
The concerts in Chicago really bring the city to life in the summer. Good luck snagging tickets though they sell out fast.
Shop
I’ve scored some great finds while shopping downtown. Even though major of the shopping in the city is lined with luxury designer stores and my wallet doesn’t allow for it it is still fun to browse the displays and I mean a little window shopping never hurt nobody.
Michigan Avenue | Magnificent Mile
A mix of higher end retailers can be found here from Tiffany’s to Burberry. Considered the Fifth Ave of Chicago.
Water Tower Place
A high rise mall on Michigan Ave with over 100 stores for all price ranges.
State Street
In the middle of all the action of downtown, you’ll find stores like Forever 21, Nordstrom Rack, Sephora and others on this busy road.
Where to Stay
Chicago has a lot of stunning and luxurious hotels to chose from. Considering I am from the area I have not had the opportunity to stay in as many as I would like but there are still a few I can recommend from experience and others I’ve discovered from hearsay from others.
+The Thompson Hotel Chicago
I stayed here for New Years a few years back. A stunning hotel that is on the smaller side. It has a beautiful lobby and restaurant inside.
+Sable Hotel
The latest and greatest new hotel in town that sits right on the water. Watch boats passing by right outside your hotel window.
+The Peninsula Chicago
I have heard amazing things about this hotel. The lobby is grand and they are really accommodating to everyone’s needs.
+Waldorf Astoria Chicago
A very pricey stay but if you can afford it you’ll be living in luxury. The entrance looks like something straight out of a movie.
Have I convinced you to visit Chicago yet? Recapping all these has be itching to explore even more of the city and find new hidden gems. I will be sure to report back. In the meantime, comment down below if you’ve been or are from Chicago and what your favorite places are. x
