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Last Updated On: October 6, 2018

If you are visiting Chicago for a few days or need help planning your Chicago vacation, this Chicago travel guide will help you see the best of the best throughout the city. Ladies, this is the perfect guide to help you plan a great Chicago trip for you and your girlfriends or for your significate other.

There is so much to see and do in this city but I’ve narrowed to down to 20 plus things you must see and do while you are in the city and I will tell you why you should skip some things because you don’t want to miss out on something really great if you are only here for a limited time.

Skip the Sears/Willis Tower and head to the Hancock Building

I’ve been to both observation decks and I love the Sear Tower, it’s a beautiful building, but if you have to choose to go to just one, you have to go to the Hancock Building. First, of all the view is just better, it’s less expensive to go up to the observation deck, and I highly suggest getting a cocktail in the Signature Lounge.

Skip the Ghost Tour and do the Gangster Tour

I’ve done both and the gangster tour is just super cool. I actually learned so much I didn’t know about Chicago gangsters along with Chicago history and fun Chicago facts that I didn’t know about.

The Chicago Riverwalk

Chicago’s newest attraction the Chicago Riverwalk is a must! It’s such a beautiful part of the city and it’s a great place to take a stroll along the river, take some photos, and enjoy a glass of wine at City Winery while you are people and boat watching.

The Best Rooftop Bar

I love a great rooftop bar and I’ve been to almost all of them in the city. There are so many amazing ones that have delicious drinks and a great atmosphere but if you want to go to a rooftop to get the best view, head to Cindy’s at the Chicago Athletic Association Hotel. Get there early to avoid the line and the crowds.

Check out this list, For The Best Rooftop Bars in Chicago!

Skip the Nutella Cafè and go to Eataly

Eataly is so much fun! There is also so much to see and do. Eataly has lots of yummy foods and restaurants, and they have a Nutella bar right inside Eataly where you can enjoy an amazing Nutella crepe and not have to wait in line.


Avoid Navy Pier and enjoy Millennium Park instead

Navy Pier is really nice and it’s great for children and families but if that’s not you, skip it and instead enjoy Millennium Park. You can feel like a kid and take a selfie at The Bean, walk around the gardens, have a picnic, and enjoy live free music concerts and movies.

For the best deep dish pizza go to Lou Malnati’s or Pequods

I know everyone has their favorites but I’m sorry if you want the best deep dish go to Lou Malnati’s or head to the Lincoln Park neighborhood and go to Pequods. Deep dish is the best if you get just cheese.


Taking the Water Taxi to Chinatown is a must-do during the summer

Taking the Water Taxi to Chinatown is an inexpensive and great way to enjoy a boat ride down the Chicago river. An all day pass is just $10. You can hop off at the end when you get to Chinatown. Walk about 5 minutes to Chinatown and explore with a delicious bubble tea.

Movies in the Park or Music in the Park?

Both are huge to Chicagoans and both are so much fun. But, if you don’t have time to do both I say go enjoy music in the park at the Jay Pritzker Pavilion. It’s less crowded and truly magical!

If you want to see a Chicago sports team, the Cubs is a must!

I’m a fan of all Chicago sports teams but if you want what I think it’s the best experience you have to go to one of the oldest stadiums in the U.S., Wrigley Field. The energy is amazing, the stadium is so beautiful, and it’s perfect on a summer day to go and enjoy a beer and a Chicago style hot dog (no ketchup!)

Head to the West Loop to indulge in some of the best restaurants in the city.

Chicago is known for great food and amazing restaurants. It’s hard to choose where to go and where to eat but if you have a limited amount of time in Chicago, head to the Randolph Street in the West Loop. You can’t go wrong with really any of the restaurants you choose.

For the best steak in the city go to Mastros

Again, Chicago has many amazing steak restaurants in the city as well but my personal favorite is Mastros. If you go, you should order the filet medium rare, and get it Oscar style. You have to get either the loaded potato or the lobster mash and be sure to save room for the butter cake.

If you want to take some amazing photos of Chicago, head to Olive Park

I recently discovered Olive Park and I’m so glad I did! The views are gorgeous! It’s a great place to take some photos of the skyline, the Lake, and the beach. It feels like a little-hidden gem in the city.

Michigan Avenue has the best shopping

Chicago does have many amazing shopping areas and there are some adorable boutique in neighborhoods all over the city but again if you have a limited time, there is nothing like shopping on Michigan Avenue any time of the year.

For the jazz in the city go to Andy’s Jazz Club or The Green Mill

You can feel like you went back in time and enjoy some local jazz music. If you are downtown you can go to Andy’s Jazz Club or if you want to head into one of Chicago’s neighborhoods go to The Green Mill.


Don’t go to Michael Jordan’s Steakhouse on Michigan Ave for dinner, instead, go underneath Michigan Ave. to Billy Goat Tavern

You have to go to Billy Goat Tavern for their famous cheezborger and chips. Billy Goat Tavern is actually located underneath Michigan Avenue. To get there, just go down the steps by the Wrigley Building, you will see a sign on where to go.

Walking the Lakefront is a must

It really is! The Lake never gets old for us Chicagoans. You can even enjoy a nice walk along the lakefront even during the winter, just make sure the sun is shining so it doesn’t feel as cold.


Lincoln Park and Lincoln Park Zoo are beautiful and they are free!

Yep! Lincoln Park Zoo is one of the only free zoos in the U.S. The zoo is located in the middle of Lincoln Park Zoo which is a beautiful park that you should definitely walk through to get to the zoo.

The Shedd Aquarium and the Art Institute of Chicago are a must

All the museums are great in Chicago but if you have a limited amount of time I think the Shedd Aquarium and the Art Institute are the best.

Don’t go to Rock N’ Roll McDonalds, go right across the street to Portillo’s

You can go to McDonald’s anywhere so skip Rock N’ Roll McDonalds and go to Portillo’s for a yummy Chicago style hot dog and the best chocolate cake! (Well, currently the Rock N’ Roll McDonalds is being remodeled into a new concept, either way going to Portillo’s is a must.)

The Langham and Shanghai Terrace are both amazing lounge bars to get a really nice cocktail

If you are looking for a really nice bar to grab a fancy cocktail I suggest going to The Langham during the colder months and Shanghai Terrace during the summer months. P.S. the brand new Zbar rooftop just opened at The Peninsula Hotel and it’s at the top of my summer list as well.)

Garrett’s Popcorn is ok but getting a donut at Stan’s Donuts is better

I don’t understand Garrett’s Popcorn thing? Sorry, Garrett’s! It always smells amazing but if you are going to have the calories then I think getting a donut at Stan’s is just better.

If you are craving good Italian food skip the wait at Quartinos on State Street and go across the street to Osteria via Stato

If you walk around North State Street it’s hard to miss the Italian restaurant, Quartinos. The patio is usually packed during the summer and it’s fun and the food is good but Osteria via Stato is really great and there’s hardly ever a wait. Everyone goes to Quartinos but I think the bread and garlic oil for dipping alone are worth going to Osteria.

Click on the image below and download and save the checklist that I created to help you plan your next vacation to Chicago.


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Girl's Guide Chicago