Where I Went In Chicago

I recently visited Chicago for the first time and managed to cram A LOT in a short amount of time. Before heading to Chicago I did some research and read about places that weren’t worth going to and places totally worth checking out. So, I’m here to share those places with you. My friend and I had some unexpected expenses we had to pay for because very intelligent us (sarcastically speaking) accidentally booked our return flight to DFW in the year 2020, no biggie (insert rolling eyes emoji here lol). So, with that being said we had to budget, but for the record, I’m all about balance while traveling. Food is a big expense and so I like to keep breakfast and lunch simple and go big on dinner.

*Read more on how crazy our trip went by heading to friends Jazmine’s blog here.

Chicago is known for having a Midwest personality with big city vibes—the best of both worlds if you ask me. Although composed of several different neighborhoods, the majority of these Chicago spots are walking distance from one another or minutes using the train. Whether it’s a five- or 45-minute long walk, you’re bound to discover tons of gems along the way. I’m always looking for new spots to explore so please let me know if you have any Chicago favorite spots!

Below I’ve listed all the spots I visited and places I stayed at.

Hope you enjoy!

Places we stayed:

Chicago Gateway Hostel

I’m not big on the whole booking a lavish hotel just because I’d rather spend that money on activities and food instead. Plus I’d only be at the hotel to sleep so it’s just not a concern for me to have the best view in the city and yada yada… So my friend and I decided to stay in a hostel. The best way I can describe what a hostel is, it’s like a college dorm. So, for the low you can book a room where you’d sleep with people you don’t know or you can book a private room and stay with your travel buddies. The thing about this is there is no restroom in your room and the restroom you do have is down the hall and being used by everyone else in that building. Unless you live in an upgraded private room where you have your own restroom but if that’s the case might as well stay in a hotel… The great thing about a hostel is 1. the experience 2. you get free breakfast and 3. they have this massive kitchen that you can go into and just whip up some food.

Here are some photos.

The Inn of Chicago

Now, the only reason why we decided to get out of the hostel was because that hostel, in particular, the water coming out of the shower head was so light and it just felt like I wasn’t cleaning myself well enough lol. Plus we kinda wanted our own shower and to stay a little closer to downtown Chicago and to top it off it was a weekday so the cost to stay in a hotel was cheaper than usual. So we did it!

Here are some photos.

Cutest photo spots:

  • Chicago Riverwalk: E. Wacker Dr Chicago, IL 60601
  • Big Monster Door: 21 S Racine Ave, Chicago, IL 60607
  • The Adler Planetarium *We didn’t go to the planetarium, this address just has a beautiful view of the city : 1300 S. Lake Shore Dr. Chicago, IL 60605
  • The Bean: * Inside Millennium Park: 201 E. Randolph St. Chicago IL 60602
  • Gallager House: *Due to the neighborhood of this address aka South Chicago (very known for crime rates) Do not go alone & do not go after midnight: 2119 South Homan Ave Chicago IL

Best places to eat:

  • Hampton Social: 353 W Hubbard St, Chicago, IL 60654
  • Riva on Navy Pier: *Anything at the Navy Pier really, this place just had the best view: 600 E. Grand Ave Chicago IL 60611
  • Cindy’s Roof Top: 12 S Michigan Ave, Chicago, IL 60603
  • Lou Malnati’s Pizzeria: There’re a few locations, find your nearest one.

Check out these bars:

There is a whole strip of bars on Addison and Clark Street. You can’t miss it because the Wrigley Stadium is right there.

  • El Hefe *Fave bar: 15 W. Hubbard St Chicago IL, 60654
    • If you check out El Hefe make sure you stop at JoJo’s Milk Bar for some good dessert: 23 W Hubbard St, Chicago, IL 60654
  • Replay Lincoln Park: *This is a chill & game bar: 2833 N Sheffield Ave, Chicago, IL 60657

Check out this Museum:

Places I wish I could've gone but didn't have time to.

  • 360C Observation Deck: 875 N. Michigan Ave, 94th Floor, Chicago, IL 60611
  • Willis Tower: 233 S Wacker Dr, Chicago, IL 60606
  • Blue Door Kitchen & Bar: 52 W Elm St, Chicago, IL 60610
  • United Centre: * MJ Statue: 1901 W Madison St, Chicago, IL 60612
  • North Avenue Beach: 1600 N Lake Shore Dr, Chicago, IL 60613

Now, that you’re done reading about where to go. The best and cheapest way to commute around Chicago is mentioned on my friend’s blog. So make sure you stay educated before you head there and most of all, have fun!

Click here to check out her blog.

P.S. I really hope this helps you and if you know anyone that’s going to Chicago send them to my blog. I’d really appreciate it 🙂

XO,
Milly