I Spent a Week in Chicago, Here’s What I Did

Travel Guide to Chicago, Illinois

Chicago is a very interesting city. My first impression I thought: “This is … different.” It wouldn’t be first on my list of top places to visit but it turns out this city turned out to be different in a great way. It’s called “character”.

My visit  to Chicago is what ultimately inspired my new USA Travel Bucketlist. I did not realize that the United States really had some hidden gems!

What I Loved About Chicago

What I loved most about Chicago was the location. Chicago is on the shores of one of the five Great Lakes, Lake Michigan. The parks and “beaches” next to these lakes are a great way to diffuse from a hectic day in the city. It’s like central park in New York, you get the best of both worlds: nature and city.

How to Get There

Multiple airports surround the Chicago area: Chicago O’Hare Airport (ORD) & Chicago Midway Airpot (MDW). Search for booking to each one and determine which one is cheapest leaving your home town.

I landed at O’hare and took the train into the city. The train took a while but I don’t imagine it would have been any better by car. The train ran alongside traffic at first, which I thought was interesting, and there was lots of traffic at the time.

You may want to arrange for a driver with a set price in advance, I don’t recommend opting for a ride-sharing app.

Where to Stay

Hyde Park – This trip I stayed in Hyde Park the college area next to the University of Chicago.

Downtown – When my mom visited she spent her time in a hotel down which has easy access to anywhere you may want to go. The instant gratification is real here.

When To Go

Winter – If you are not used to it, don’t make the mistake and go during the winter months. Chicago winters (although it is off season) are known to be frigid.

Summer – I visited in the summer and I got lucky. I had perfect 70 degree temperatures with sunny days and cool winds coming off the lake.

How to get around

Bus Pass – Always a smart option in big cities. Get where you need to go and maybe even receive discounts for other attractions within the city.

Uber/Lyft – This is big in any city but the best part is when they offer pool, a much cheaper alternative.

Walk – In Chicago all the attractions seem to be in a long line down the “coast”. walking is probably your best bet in order to see and explore this city.

Things to Do

Hyde Park

Promontory Point – This park area is very close to Hyde Park. The entire area was filled with green grass and wildflowers meanwhile you can hear the wave’s crashing on to the concrete shore haha. I am always lucky with weather so this was really a beautiful way to begin my day.

Barack & Michelle’s Old House – I was visiting my sister who lived in Hyde Park  so she told me about this little gem. Nothing but 2 blocks from where we were staying i got to see where Michelle and Obama spend their days before they moved to the White House. I felt super close to history and I absolutely loved it. Close by is the Dunkin Donuts where they first met and it’s immortalized on a cute little monument outside the store.


Buckingham Fountain//Grant Park – Definitely recommend you begin your walk in grant park. The beautiful fountain there is very grand. The park is also filled with beautiful flowers and serves as a place for many events. At the time of my visit they were preparing to host EDC.

Millenium Park (The Bean) – If you have it in you keep walking and you’ll hit the tourist trap at Millenium Park where you can find the infamous Bean.

John Hancock Center – Just before you hit the Magnificent Mile you can stop at the John Hancock Center for free amazing views of the city and lake. You can also have dinner or drinks with a view in this building.

Weird Little Fact: If you are a woman you can also enjoy floor to ceiling windows unobstructed views from the ladies restroom.

Magnificent Mile – Once you’re done eating or drinking if you still have it in you, you can continue walking until you reach the beginning of the Magnificent Mile. It an area filled with all the shops you can imagine. From fast fashion giants to Chanel it’s all there.

Oak Street Beach to North Avenue Beach – On a another day I  would recommend relaxing on one of the lake’s beaches Chicago has to offer.

I chose a day and walked from Oak Street Beach to North Avenue Beach If I remember correctly Oak Street Beach had a younger, lively, active crowd. The beach is filled with volleyball courts and music, if that is your sort of thing.

If you want something I bit more relaxed I would suggest North Avenue Beach which does not have a proper shore or sand but it is coupled with a park and expansive green space for a picnic, tanning, or laying around reading a book which is what I opted for.

Lincoln Park Zoo – This is actually another free activity. This was my first time visiting a zoo and all I can say is it was interesting. I’m not sure I am a fan of Zoo’s, however, if this suits your fancy there’s no problem here. It’s also great for the family.

Chicago Theatre – Did not go inside, this was definitely just one for the gram. Great Instagram photo op.

Willis Tower – If you’re looking for an adrenaline rush in the city I would definitely recommend you visit Willis Tower. A pricy attraction with long lines but I think it was pretty worth it.

Of course you can pay for a fast track, however, the wait was worth it and the views were amazing.

Things I did not get a chance to do but I recommend you try:

Water Taxi

Navy Pier 

Field Museum

Where to Eat

I was lucky enough to have a place to stay where I could cook and be cooked for so not many suggestions here but I hope you enjoy these few breakfast recommendations:

Hero Coffee Roasters

Wildberry Pancakes & Cafe – Great, this seems to be very popular and has long waiting times (being in the middle of the city) however,

YOLK was better. I tried the potato scrambles at both and Yolk was really amazing. It’s also worth the money, I feel like we got so much for our money.

Chicago Deep Dish Pizza Yes I did also try Deep Dish pizza’s from TWO different and I am not a fan. So no recommendations here either.

I thought third time would be the charm but I did not get the chance to try Chicago Piza and Oven Grinder Co. Why? Watch out for their hours of operation.

The End

That’s all folks. I hope you’ve enjoyed the City Guide to Chicago, Illinois. See ya next time for the next adventure.

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10 Things to Do in Chicago, Illinois: A comprehensive city guide including where to eat, where to stay and how to get there. #chitown #hiddengems #USA


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