Tips for your first trip to Chicago

10 helpful tips to guide your trip

Guest post by Lizz Riggs

Chicago is a city full of exciting things to do; full of history and culture. Everybody who comes to Chicago for the first time wants to do it all, but it’s hard to fit everything into one trip. There are some things that just can not be missed — keep these in mind when you’re planning your trip!

Stay downtown.


1Many people think that they have two real options: they can either stay in one of the hotels in Chicago near all the best things and pay a fortune or they can stay far away, commute and still be able to afford their next meal. This is simply not the case. First of all, there are plenty of inexpensive hotels in Downtown Chicago that are still clean, safe and convenient. Many of the less expensive ones also offer great Chicago hotel deals and packages throughout the year though, which will help you save. Many package deals include free meals and admission to popular attractions in addition to great room prices. Be sure to do a little research before booking a hotel that you won’t love.

Pack for the weather

2Chicago temperatures can be pretty extreme. When you’re visiting in the winter, bundle up good so you don’t have to sacrifice any fingers to frostbite just to get picture of the Bean. The summers can also get sweltering hot, so don’t pack just jeans and expect to be comfortable on your vacation. While the temperatures range for very high to very low, as long as you pack appropriately, you’ll be ready to live it up happily in the Windy City.

Visit the Hancock Observatory

3This is by far the best view of Chicago, and while you’re up there, you can also head for some pricey cocktails at the Signature Room while you continue to enjoy the views.

Check out at least one museum


4There are so many great museums in Chicago, whether you’re into history, science, art or animals. Many of the museums are centrally located, whether it’s Downtown or on Museum Campus, so getting there is hardly an issue.

Know what you’re getting into at Navy Pier

5 The views are beautiful, but any pictures you take during the popular seasons are going to be jam packed with people. The food is good, but it’s generally pricier than the food you’ll get elsewhere. Navy Pier is a tourist trap, so don’t expect anything less. But that doesn’t mean that you should avoid it at all costs, because it is one of the most beautiful sights in Chicago for a reason!

Take in the sights on a tour of Chicago

6It’s hard to see all the things you’re going to want to see on your own, but Chicago tours give you a great all around experience and take you to almost all of the popular sights you’ll want to see in just a few short hours. Then you can always go back for a more in depth experience at the museums and attractions you want a better look at later.

Pack your camera

7Of course, no brainer. But be sure to bring it with you every time you go out. Whether you’re going on your tour or heading out to dinner, some of the best views of Chicago come in the most unexpected places when you least expect it!

Don’t eat just pizza


8Sure, Chicago is known for the deep-dish pizza, but there are tons of other great foods here. Chicago-style hot dogs, Italian meat and seafood are all big hits in this city. Check out one of the famous restaurants, or a whole in the wall joint, and you won’t be disappointed you didn’t get another pie this meal. But hey, you can’t go wrong with the pizza either!

Try some locals brews

9Chicago has so many local breweries, and you can head to one like Revolution Brewing, Goose Island, Half Acre and Atlas Brewing are all popular breweries that you can visit, but you can also sample many of the local craft beers at bars and restaurants around town. You should definitely try at least one while you’re here.

Don’t think you can’t go to Wrigley when it isn’t baseball season

10There are tons of things to do at Wrigley Field, whether you’re going for a game or not. Check out the souvenir shop, take a tour or grab a dog, a Bud and cheer on the Cubs. The historic Wrigley Field is open year-round for people to visit.

Some of the best things to do in Chicago include sightseeing, shopping and eating yourself into the next size up, but visiting this city is a balancing act. Save time, money and room for more delicious local fare by preparing a little and knowing what to expect from the beautiful Windy City!

Lizz Riggs is the editor of

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