Windy City - 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.

About Chicago

Trains: Chicago Union Station, started in 1913, is one of the most beautiful train stations in the country with its large barrel-vaulted Great Hall. It is one of the biggest train hubs in the country uniting the four railroads at the time: the Pennsylvania Railroad; Chicago, Burlington and Quincy Railroad; Michigan Central Railroad; and the Chicago, Milwaukee and St. Paul Railway. Union Station is the only example in the United States of a “double-stub” station, where the train tracks travel in two different directions from the station.

Flights: Fly into Chicago’s O’Hare airport, one of the busiest airports in the U.S. which is also full of colorful art. Wander beneath the longest neon sculpture in the world down the walkway between concourses B and C.

Local Transportation: Take the CTA line around the loop to get further outside Chicago, or ride the light blue Divvy bikes where you need to go.

When to visit: Visit Chicago between April and May or September and October for warm weather and fewer crowds. Summer is the most popular time, but prices are better just before or after summer months.

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.

Make sure you stay educated before you head there, Click here to check out my friends blog, so you can get some more detailed information on how to get around the city.

If you or someone you know is taking a trip to Chicago and needs help on where to go or what to do. Feel free to check out my Travel Guides where I give you all the cool spots to take pictures, where to eat, where to go and so much more! You can even purchase a custom travel itinerary where I make your trip a WHOLE LOT SMOOTHER (must be purchased 3 weeks before trip).

Click here to purchase my travel guide.

XO, Milly


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