Best City in the U.S. Chicago

If you haven’t heard yet, Chicago was voted Best City in the U.S. in the Condé Nast Traveler Readers’ Choice Awards for the second year in a row! Having visited Chicago a couple times myself I can say I agree with this amazing city being top dog two years in a row. I decided to put together a short guide of hopefully useful information to help you plan your trip to this remarkable city.

Getting to Chicago

Chicago has two major airports; Chicago Midway International Airport (MDW) and Chicago O’Hare International Airport (ORD). I personally prefer Midway, it’s a smaller, but a really nice airport. I’ve never encountered any issues flying in or out of Midway. You can also catch the Orange Line “L” train directly from Midway and it will take you directly into “The Loop” in Downtown. If you choose to fly into O’Hare you can also catch the “L” from the airport except this will be the Blue Line. It will take you into Downtown as well, just hop off at Clark/Lake.

Getting Around

The “L”

I mentioned the “L” in the previous section but I’m going to talk about it some more. The “L,” which is short for elevated, is Chicago’s rapid transit system, it serves the city of Chicago and some of its surrounding suburbs. It uses colors to identify each of the lines. There are eight lines in total and they are; Red, Orange, Yellow, Green, Blue, Purple, Brown and the Pink Line. The “L” is probably the fastest, cheapest option if you are looking for public transportation. The “L” uses the Ventra card which you can purchase at any station. A one way ticket will run you $2.50. If you plan on taking the “L” numerous times while you are in the city you can also purchase a 1-Day, 3-Day, or 7-Day pass. You can also hail a taxi, use Uber or Lyft. I love getting the feel for a city by walking. Chicago was no exception to that, I walked EVERYWHERE! So needless to say, Chicago is a very walkable city, weather permitted of course.

Where to Stay

There are plenty of options in this city. I recommend staying in the Loop or somewhere in Downtown, it’s a pretty central starting point to explore. I’ve stayed at the Hyatt Regency Chicago and most recently at The Westin Chicago North. Both were fabulous hotels, I had a great stay at both hotels, they’re centrally located and I could walk to almost everything I wanted to do/see.


Chicago gets to experience four distinct seasons. I’ve visited in the summer, which can be very warm and humid, like LA hot and humid. Temperatures can often exceed 90 degrees Fahrenheit. When I was there in July, it was in the 80s and 90s and it was only humid a few days, which was nice. Winters are generally cold and snowy. You can also get sunny but snowy days as well. I’ve always wanted to visit during winter but I’m a spoiled LA girl who probably couldn’t handle it. Spring and Fall are mild seasons typically with low humidity. I was most recently in Chicago in March 2018, it was cold, low to mid 30s, but surprisingly comfortable until the wind came ripping around the corners of buildings. The wind in Chicago is no joke people! It’s called the Windy City for a reason.

What to do

There is so much to do and see I don’t even know where to start! 360 Chicago and Willis Tower provide fantastic views of the city, each offering a different take of the city. I liked 360 Chicago a little bit more but both were great to experience. There are numerous museums, you should be able to find something for everyone! My personal favorites are: The Art Institute of Chicago, Adler Planetarium, and Museum of Contemporary Art Chicago.There’s also Shedd Aquarium, Millennium Park, Cloud Gate or the Bean, Grant Park and Magnificent Mile. If you’re visiting between October and May head over to City Winery and check out their domes or igloos as I call them. Walk the Riverwalk or enjoy an afternoon tea. Just wander around the streets of Chicago and you’ll find something that catches your fancy.


The food and coffee scene here is unreal! I still have a very long list of restaurants/coffee shops I’ve yet to make it through. Some of my favorites include: Giordano’s, Wildberry Pancakes and Cafe, Public House, XOCO by Rick Bayless, Firecakes Donuts, Park Grill, Cindy’s Rooftop, Goddess and the Baker, Eataly. You can read my past posts on these places here and here.

I fell in love with Chicago the second I got off of the Orange Line. The history, architecture, food, coffee and the people make it easy to love. I often find myself wishing I were back in this magical city and find myself trying to find an excuse to go back. I’m hoping with this guide I did Chicago justice and I’m hoping after you read it you’ll want to do more research and start planning your own trip. 

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