In my 10 Tips For Cheap Travel post, I talked about how to find cheap tickets online for some affordable getaways. While following my own advice, I found some amazing cheap tickets to Chicago from Washington, DC, for $49 each way. I was sold! I had never been to Chicago before and I thought this would be a great opportunity for the first Solodolo adventure. Prior to my trip, I looked up things to do in Chicago to get prepared, but as I've advised, I didn't pre-purchase any activities. When I landed in Chicago I asked my Lyft driver about where I should go, and began my adventures from there. To sum up my trip:
I Spent Less Than $300
- $90 for the ticket from Southwest.com
- $93.92 for room and board at IHSP hostel, which I booked through hotels.com
- $100 for food, fun and transport
- I took the subway which they call the "L" but it wasn't the fastest way to get around
- I walked A LOT because everything was only a few miles apart
- I used Lyft, because they had some awesome deals there! Sometimes my trips were as low as $3!
Sumertime Chi is the S**T
I spoke with some Chicago residents and they all agreed with my initial research - only go in the summer time. Apparently the winters are brutal and I'm glad I took this opportunity in the summer time! Because the winters are so awful, Chicagoans take full advantage of their summer time, especially on lake Michigan, which is absolutely gorgeous. I never knew lake water could be so clear. The weather was beautiful, not too humid and there was a nice little breeze throughout the days. (Chicago is known as the windy city but not because it's windy, but rather because of politics and something about the hot air politicians blow, or something like that). Summertime is definitely the best time to go.
Scalp Cheap Tickets To a Cubs Game
As soon as I landed, I dropped my belongings off at the hostel, and took the L to Wrigley Field, where the Cubs baseball team plays. I got there at the top of the 5th inning, scalped a $10 ticket and it was totally worth it! I know a bit about baseball, enough to have a small conversation about it, but even if you don't understand or love baseball you must go. I have never experienced a baseball team with such adoring and fun fans in my life! The fans sang, cheered and even danced! Of course it helped that the Cubs were up by 6 whopping points but I have a feeling they are always this excited about their home team. The later it is in the game, the cheaper the tickets get, so don't be afraid to go late. Make sure you also get a hotdog Chicago style with the peppers, it's delicious! After the game I walked over to the Cubby Bear, an enormous bar right around the corner to celebrate the win the Chicagoan way. Everyone was super nice and the prices were very affordable.
Deep Dish is Overrated, But Try It!
When you think deep dish, you think Chicago; so I had to try the deep dish pizza, and it was forgettable. Deep dish consists of a deep bread base, toped with sausage, cheese or pepperoni, and then another layer of bread and then more cheese and toppings. I could only eat about half of it but I'm glad I tried it. Now I don't ever need to wonder what it's like or talk about it again.
The Art Institute is a Must
I spent a few hours at the Art Institute but couldn't see the entire exhibit - it is massive. This art museum holds some of the most famous pieces of art from around the world, with everything from classic to contemporary and historical. A few tips for ensuring you have a great time: they have a student discount, get there at least 30 minutes early in the morning because there is a line, you can't carry your bag around but they have a bag and coat check for $1, and you won't get to see everything in one day, so you may want to plan another visit. The famous Bean structure was on the way, so of course I stopped there and even had lunch at a farmers market along the way.
See 360 Views For $15
Most people go to the Sears Tower's Observation Deck for a 360 degree views of the city. The Deck is made entirely of glass and not recommended if you are terrified of highs. However, there is a different way to get a 360 degree view of the city without purchasing a ticket to the Deck or waiting in line - The Signature Room at the John Hancock building. This is a chic restaurant and lounge on the 95th floor of the building. Not quite as high as the Sears Tower but still spectacular. Best part is that it is much cheaper and more comfortable than the Observation Deck. Go up there, prepare for your ears to pop on the elevator, order a drink and sit by the window and enjoy the view. Every seat is a great seat though so even at the bar you'll see the spectacular views. The drinks are a bit pricey, similar to DC and New York prices, but the view and atmosphere is totally worth it. The food wasn't so bad either.Walk to the Beach and Lake
My last day in Chi-town I spent at the beach and lake. I walked from my hostel to the beach which was about 4 miles and then from there to the lake which was another couple of miles. There are bike rental companies if you prefer that, but walking was great exercise and allowed me to see a lot of the city. The walk to the beach was gorgeous and then around the bin to the lake was even more beautiful. I met up with a friend for a boat day on lake Michigan, swam and had a blast. The water was cool and clear and for a DC resident this was a great treat. Many others were out there on their boats as well, anchored and enjoying the weather. I only wish I could have gone during one of their boat festivals when apparently the boats tie up to each other and it's an enormous party. If you don't have a friend with a boat, there are many boat rental tours that are just as fun as well.I had an amazing time in Chicago and I would definitely go back! Share your experience.

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