Chicago Travel Guide

I spent most of the summer traveling, and had so much fun! One of the places I visited was Chicago for Lollapalooza, and it was such a great time. I’ve decided to share a Chicago travel guide of my favourite things to see and do, where to eat, and where to stay, based on my last three trips to Chicago. Keep reading for my Chicago travel guide.

Where to Stay:

I have visited Chicago three times in the past two years, and have had a great experience at all the hotels I stayed at. I stayed at theWit Chicago, Hyatt Place Chicago/Downtown – The Loop, and Sheraton Grand Chicago.

theWit – 201 N. State St, Chicago

Of all the hotels I stayed at in Chicago this is by far my favorite. Great location, great rooms, great staff. We were upgraded to a suite and the room was AMAZING! It had river views, and was located right downtown, so you could explore the Loop and walk across to River North very easily.

Hyatt Place Chicago/ Downtown – The Loop – 28 N. Franklin St, Chicago

Next up is the Hyatt Place Downtown. We stayed here for Lollapalooza and were really happy with it. It is a short walk to West Loop, River North and minutes to downtown Chicago. It was in a quieter location, so if you like to stay somewhere quiet but close to the hustle and bustle I would recommend staying here.

Sheraton Grand Chicago – 301 E N. Water St, Chicago

Lastly we have the Sheraton Grand Chicago. I stayed here on my very first trip to Chicago and couldn’t love the location more. Close proximity to Magnificent Mile, Navy Pier, and Millennium Park made it the perfect location to walk everywhere!

Where to Eat and Drink:

Au Cheval burger and fries

Au Cheval has one of the best burgers! We were able to walk their from the Hyatt Place and it was in the cutest neighborhood. The burger is incredible and the fries were also amazing, they came with an egg on top and are the perfect brunch food. There was a wait when we got there 10 minutes after it opened, so I’d recommend getting their early.

Al’s Roast Beef is a must visit, and my number one recommendation for food on my Chicago travel guide. They have a few locations around the city, and their roast beef sandwich with gravy is to die for.

Lou Malnati’s is a Chicago institution, best known for deep dish pizza. We tried both of their specialty pies and they were delicious! Make sure you go when you’re hungry because it’s sure to fill you up.

If you’re looking for a crazy milkshake, look no further than Jojo’s Shake Bar. This crazy little cafe has crazy shakes that are incredible, and are more of a meal than a dessert!

If you love cupcakes, then you have to go to Molly’s Cupcakes! So many fun flavors and they are absolutely delicious.

Can you tell I love dessert!? Yet another dessert recommendation – Dessert Dealer at Parlor Pizza! They have ice cream tacos and fried ice cream, which were both delicious. Parlor Pizza is also really good for some pizza and drinks.

If you’re looking for a fun bar, you need to go to Three Dots and a Dash is for you! It is a really fun tiki bar with amazing drinks.

If you take one thing away from this Chicago travel guide, let it be this – visit all the rooftops! London House Rooftop was our favorite, it had the best views of the river and the city. theWit also had a really nice rooftop.

What to Do:

Chicago is big on sports, so going to a sports game is always something fun to do! I have been to two Cubs games and it is so much fun to visit Wrigley Field, and the area surrounding it, Wrigleyville is also fun to visit!

See Chicago from the sky and visit the Sky Deck. It’s a cool experience and provides a good photo opportunity.

Visit Navy Pier! Navy Pier is a really fun area to walk around and grab some drinks and food. Theres always something going on there!

Visiting the Bean in Millennium Park

Visit Millennium Park and Grant Park. You can’t visit Chicago and not see The Bean! These parks are right next to each other, and are really nice to walk around.

Walking along the river front

Walk along the river front. It is such a nice walk and there are some cute restaurants and bars on the river front.

If you want to shop, head down Magnificent Mile. There’s lots of stores to wander around including all the luxury stores like Tiffany and Co and Gucci.

That’s a wrap on my Chicago Travel Guide. As always, thanks for reading!