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How to get blown away by the Windy City

If you're planning a trip to Chicago you have come to the right place! I have tips and places to go for the cold winter months as well as the summer!

Cloud Gate (The Bean)

Any Season

Transportation

Buy a Ventra card! I got a 3-day unlimited pass for about $25, and it was super useful. The transportation system in this city works very well and you can get pretty much anywhere you need to go using the trains.

Sights

1. Millenium Park- Most visitors come here to visit Cloud Gate, which is more commonly known as The Bean. It is a huge sculpture. It's best to go early in the morning before hundreds and hundreds of visitors fill the area. I took this shot at about 7:30-8am on a weekday. If you go any later, that ground will be filled with hundreds of people.

2. Willis tower- Are you afraid of heights? The Chicago Skydeck has a glass floor where you can see the city 103 floors below you. We went at around 10 am (opening time) on a weekday and it was completely empty so we got to take our time with photos and didn't even have to wait in line! I'm not sure if we just came at a lucky time, but as we were leaving, the line just to get in was over 2 hrs long. Go early to avoid the wait!

3. Art Institute of Chicago- This is one of the most well-known art museums in the US. It's a great place to appreciate some wonderful art and also to escape the cold!

4. Magnificent Mile- All your shopping dreams can come true here. Take a walk along this mile of upscale shops and visit the Water Tower as well! The Signature Lounge at the Hancock Center is nearby and has some amazing views! It is also where you can do The Tilt if you're interested in the thrill of slowly falling 1000 feet in the sky.

5. Navy Pier- This is probably Chicago's biggest attractions. There's food, rides, and fun activities! TIP: There is no train stop for Navy Pier, so the best way is to take the free trolley or Uber. The trolley stops running at around 10pm, but if you Uber, know that there is a very specific pick up/drop off spot. So don't get lost for 2 hours late at night in the freezing cold like we did :')))

6. Chinatown- In my opinion, it is very hard to find good Asian food in Chicago. If you're looking for authentic food or cute shops, take a visit to Chinatown! For my favorite boba tea shop recommendation, check my Chicago Food Reviews blog post!


Winter

Packing

Chicago gets VERY COLD. I am used to winters in Georgia where just the of thought snow causes grocery stores to run out of bread and schools to be cancelled. I thought I would be prepared for the weather by wearing all my layers (2 jackets, a sweater, a long sleeved thermal shirt, a tank top, two pairs of leggings and gloves), but I was wrong. The tall skyscraper buildings around the city trap the wind and throw it at you, making it windier and colder than you would think. Dress warm.

Sights

1. Christkindlmarket- This market is only open during the holiday season and is super cute! There are rows of decorated German shops, and people sell food, drinks, and nice holiday items! I would strongly recommend!

2. Lincoln Park Zoo- This wonderful place is donation-based! During the winter season, it's a zoo by day and a light exhibit by night! The holiday lights are so nice and you can really feel the holiday spirit! 100% I would go back.

3. Maggie Daley Park- This park has a beautiful outdoor ice skating ribbon, but the line was way too long, so I didn't even try. The surrounding parks are connected and great for walking around (Millenium park, Grant park etc.)! Unfortunately, the fountains are turned off during the winter, but it is still nice to walk around!

Summer

Packing

Unlike Chicago's winters, summer is pretty hot. I wore tank tops, shorts, and summer dresses.

Sights

1. Garfield Park Conservatory- This is a donation-based conservatory filled with all the plants and greenery you've ever dreamed.

2. Chicago Riverwalk- Imagine walking along a this river on a sunny warm but breezy day while eating the perfect popsicle. So great.

3. Jay Priztker Pavillon- During the summer, there are free outdoor movies here! Bring out your picnic blanket and relax under the stars.

4. Buckingham Fountain- The fountains are closed during the winter, but during the summer, this giant fountain is really nice! If you are looking for other unique fountains, Crown Fountain is just a few minutes walk away!


I hope these tips help you plan your next trip! Looking for all my food recommendations (vegetarian and non-vegetarian friendly)? Check out my blog post on my Chicago Food Reviews!




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