Quick Guide to Chicago; The Windy City

Destination: Chicago
Travel Companion: My awesome Dad
Duration: 4 days
Budget: $650 pp (excluding flights; FYI internal US Flights are around 200$)

Chicago was such a pleasant surprise. I've been traveling to the U.S. for over 12 years now, and visiting at least once a year for the past 6 years. I've been to 5 states so far. So I decided to start exploring more of the U.S. and visit a new state, after all, this is a huge country with a lot to see! I picked Chicago because a friend lives there and suggested I check it out, moreover it was one direct flight away for both my dad and myself. So I went for it!

The Cloud Gate aka Chicago Bean - Millennium Park

Chicago definitely exceeded my expectations, even though the weather wasn't very nice to us and my dad and I had only packed t-shirts only with just one hoodie, yet we still made it work!

Anyway, here's a quick guide to things you can do in Chicago! If you're ever in the U.S., do check it out. I can easily say Chicago is one of my favorite American cities so far.

1) Where to stay

Stay in Downtown, it's as simple as that. It's super efficient and easy to just be close to everything. It will be more expensive (accommodation in general is not cheap in Chicago), but you'll save on transport and time much more. I stayed on North DeWitt Place, it was slightly out of the crowded streets, but only few minutes walk away from the center.

Beautiful Church on Michigan Avenue - Chicago

Our friends have a very nice view!

2) How to move around

I do not recommend renting a car because daily parking will cost a tonne, moreover it is extremely difficult finding a parking spot, so you'll probably end up parking it somewhere and then taking public transport to move around.

In terms of transport, you can go by: Train (accessible from the airport), Uber (I used UberPool Express - saved quite a bit), bus, segway, bicycle (there's a lot of those bicycle rentals on the streets) and even a horse carriage! You can also hop on the hop on hop off bus. If you're taking a taxi back to the airport, keep in mind that rush hour is between 2:30PM and 6:30PM and it will take over an hour.

3) Things to do

  • Watch a Baseball game. You just gotta experience it. It's more of a family / friends hang out, eating a hotdog, having a drink, eating nuts or popcorn (did you know that the first popcorn machine was made in Chicago in 1885?) and just enjoy the home runs when they happen!
  • Go on a Historical or Architecture River Tour, includes a visit to Lake Michigan. It's really something you have to do as architecture is quite impressive in Chicago, after all they say Chicago is the best architectural city in the U.S.
  • Watch a Comedy show at Second City (did you know that a lot of Saturday night live comedians started out there?)
  • See Chicago from up high by either visiting SkyDeck (and standing on glass - scary huh!) or going to Hancock Tower's Observation Deck - 360 Chicago and tilting on the glass. A quick hack is to go up for a drink on the 96th floor to The Signature Lounge. Unfortunately it was foggy so I couldn't do either.
  • Hop on Hop off Bus - always a good idea!
  • Rent a boat and ride through Chicago River among the giant skyscrapers 
  • You can also kayak in the river.
  • Walk on The Concrete Beach by Michigan lake where you get to see a good view of  Downtown Chicago skyline.
  • Segway Tour (I would never get on a segway, but if it's your thing, why not!)
Baseball Game at the Wrigley Field - Chicago
Chicago Architecture
The Signature Lounge - 96th floor of Hancock Tower

4) Places to visit

  • The famous Cloud Gate (aka Chicago Bean) and Millennium Park. We were lucky as there was a free Blues Festival happening there, so keep an eye for festivals like that.
  • Museums (check out CityPASS for a combo ticket to different things for a good price):
    • Museum of Science and Industry; if you're there with young kids, I think they'll enjoy this quite a bit
    • Museum of Modern Art
    • The Field Museum; this was a very nice museum to visit specially if you like history, animals and dinosaurs! They have a new T-Rex on Display, called Sue!
    • Shedd Aquarium
  • Chicago Art Institute 
  • Lincoln Park Zoo
  • University of Chicago
  • Navy Pier and the Centennial Wheel which offers a good view of Chicago and Lake Michigan. The original one was built for the 1893 World's Columbian Exposition.
  • Buckingham Fountain
The Field Museum
Navy Pier

The Concrete Beach - Chicago Skyline
Lincoln Park Zoo

5) What to eat

  • Deepdish Pizza: Of course everyone is going to tell you to try a Deep Dish Pizza. And I will add my voice to theirs, the experience is quite interesting. Having said that, I tried it at Lou Malnati's (a super famous place), but I personally think it's overrated, please don't kill me, I love me a classic pizza, mostly Italian marguerita #sorrynotsorry). Maybe I didn't try a flavor I like, and perhaps I should've tried it at more than one place to be able to compare. There's also Giordano's and Gino's, as few other places you can try.
  • Breakfast Spots: Breakfast is the most important meal of the day, and I truly believe that. So here are few spots I tried and really enjoyed: Beatrix and The Original Pancake House for breakfast. Even my dad liked them, and he hates eating outside in general! A friend of mine also recommend Yolk, I didn't get to try it because when we got there there was a long waiting queue.
  • Fancy restaurants: another friend recommended Au Cheval Burger, Blackbird or Next (Michelin star diner) if you fancy!
Pancakes and Waffles!

Deep Dish Pizza - Lou Malnati's



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