What You Should Know Before Planning a Trip to Chicago

Chicago, Navy Pier

Chicago was the first American city to welcome me when I stepped on North American soil. It mesmerized me with its impressive business hotels and welcome amenities, and the city’s sights later blew my mind. I’d traveled to Chicago for business, but I made sure to visit as much as I could, often squeezing in some fun excursions. If you want to plan a trip to Chicago, here are a few things you should know as you develop your itinerary.

When’s the Best Time to Visit Chicago?

Whatever you do, avoid visiting during the winter. Chicago gets cold and windy, and the winter isn’t the best time to enjoy outdoor activities like the Navy Pier. If you have a limited budget but still want to enjoy a less crowded visit, then plan your trip during the late spring or early autumn. When I visited in May, the weather was great, but the attractions weren’t too busy just yet. The cab ride downtown was fast, the pier was empty, and we got on the Ferris wheel immediately.

Navy Pier, Chicago

Where to Stay in Chicago?

The hotel you choose in Chicago depends a lot on your budget and your reason for traveling to the third largest city in the United States. If you’re visiting on business or for a conference, consider one of the many Rosemont hotels, which are adjacent to the airport and close to several convention centers. If you’re visiting for fun, plan to stay closer to the sights. Here’s a complete guide to Chicago hotels and motels to help you out.

How to Navigate Chicago?

My trip to Chicago was also my first one over the Atlantic, so it served as my introduction to jet lag. I was there on business, but due to jet lag, I hardly had time to figure where I was and where I needed to go. As a result, I relied on taxis a lot, especially to and from the airport and the convention center. I later found out that Chicago’s public transportation network makes it quite easy to get around. There are also extensive bike lanes and water taxis, too. You can find full details on public transit fares and options here.

Chicago from the Ferris Wheel

Chicago from the Ferris Wheel

What to See in Chicago?

Navy Pier is a must, as touristy as it might be. There you can ride the Ferris wheel, which is perfect for taking shots of the skyscrapers and boats. The restaurants around Navy Pier are fun, and an evening walk through downtown Chicago is amazing. The city’s shopping options are vast, and the business-focused hotels and convention centers in Rosemont will awe you. The Art Institute of Chicago, the Magnificent Mile, Millennium Park, and the Adler Planetarium are just a few of the must-see landmarks you should visit if you have more than a few hours one evening.

Chicago by Night

Chicago by Night

Now that you know when to plan your trip to Chicago, where to go, how to get there, and where to stay, there’s only one thing left to do. Enjoy your vacation!

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What You Should Know Before Planning a Trip to Chicago

20 Comment to “What You Should Know Before Planning a Trip to Chicago”

  1. I’ve only been to the city on very short visits and haven’t really explored, though I’d love to in the future. It is good to know that the public transportation system in Chicago is comprehensive and useful and that the city is easy to navigate. The city’s setting on the lake is truly beautiful and your tips on where to photograph the skyline are helpful!

  2. Christina says:

    A friend of mine moved to Chicago a few years ago and I’ve been meaning to pop over for a visit. I guess I should go as it looks like a pretty big city with lots of things to do. Will take your advice and avoid winter.

  3. Jennifer says:

    My husband is from Chicago and his family all still live in the city. My favorite time to visit is summer since we can go to a Cubbies game and the Taste of Chicago is each July. It’s pretty much the ultimate food festival!

  4. What a comprehensive guide. I don’t have any plans to visit chicago right now, but I’ll definitely come back here if I do change my plans

  5. My husband and I have been planning to travel to the US and we keep reading great things about Chicago. It’s not a common travel destination for Brazilian, but we like to discover new places… Thanks for the tips!


    • It was my first city in the US and I loved it. My only regret was the lack of time and not being prepared for how much jet lag would suck. I couldn’t sleep on the flight, although I tried. I was too excited about my first intercontinental flight 😀

  6. Drew says:

    One of my favorite US cities. Chicago has so much to offer, and its unique, funky neighborhoods are so much fun to explore. I would agree to avoid winter, since it gets so unbelievably cold! I’ve been a couple of times in December and January, and those chilling winds whipping through the streets is never pleasant!

  7. Thanks for the great tips – I do plan to avoid traveling during the winter above all else!! I’ve heard some pretty horrendous weather tales these past few years!

    • Yes, that’s true 😀 If I have to travel during winter, i prefer going to some nice little paradise where it’s still warm. I have my own horrendous tales of winter disasters 😀 Driving for two days in a snowstorm, that kind of thing 😛

  8. Tara says:

    I love Chicago, but you’re right, it’s not much fun in the winter. I tend to splurge on downtown accommodations whenever I visit – It’s so worth it to be able to walk.

    • When it’s something I organize, I do the same. But on my trip there, it was a business thing. And the airport hotel the company chose was pretty close to the convention center where the event was. That helped a lot, especially since we had huge roll up banners and a lot of flyers to carry over there.

  9. What an amazing guide to Chicago, somewhere I have never been but it’s definitely on my list!

  10. Holly says:

    I liked Chicago. I went last summer. I would happily go back to check out a few other things I didn’t get to see.

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