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Things to Know Before Traveling to Chicago

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Chicago is a wonderful city to visit, but before you do, you should know a thing or two about the city, the best ways to get around, the best places to stay at, and a few things to do. We intend to let you know some cheap ways to get into museums, decide on the best time for a visit, and transportation you should use.

Read on and have fun in Chicago!

What is the best way to commute to and from the airports?

A new express train is currently being built for people who wish to commute from O’Hare International to downtown and back. This is great for business people. Locals prefer the old faithful Chicago Transit Authority El trains to and from O’Hare and Midway. It costs $2.50 to go to downtown from Midway and $5 from O’Hare. Not many cities have such a convenient way to get around and all for under an hour.

Should you get a CTA Pass?

Don’t rent a car if you are staying in the city, just use the CTA. It’s very easy to navigate, but it might get a bit tricky to understand the rates because there is one price for a bus, another for a train, and some fees for transfers. Who wants to deal with all that? The best option is to buy a $20 unlimited Ventra card for 3 days or $33 Ventra for 7 days and go wherever you want whenever. You can buy Ventra cards in every El station.

Is there a parking app for drivers?

If you choose to drive in the city, definitely download ParkChicago. You will have to create an account using your car tag number and link a credit card to it. Paying with this app is a breeze as you will be using parking zone numbers from street parking locations. You might find some residential streets, where parking is with permits only, and then there will be a few streets with free parking, which you should check and double check.

What is Chicago grid system?

If you are a fan of maps and find them to be the most reliable way of navigation, you are in luck in Chicago, because the city is built following the grid system. The intersection of State and Madison Street is the middle point. All the streets and blocks fan out from there in South-North and East-West directions. Every eight blocks equal a mile.

What other apps can help you in Chicago?

You should definitely use Google Maps and Apple Maps for walking directions.

Google Maps - Transit and Food App

Uber and Lyft can take you from anywhere to anywhere any time of the day. Transit app is great for buses and trains and their arrival times.

Uber & Lyft Apps

How much time should you allocate for every destination?

There are over 3 million people living in the city itself, so expect delays and allocate plenty of time just in case. This applies to highways and the El. If you have a strict appointment time, always allow extra time.

How much tip should I leave?

Chicago works the same way the rest of US does when it comes to tipping – 20% at sit down restaurants for good service, $1 per drink at the bar, and the rest is up to you.

Should I have cash with me?

It might be a good idea to have some cash with you, because you might venture into a dive bar or some cheap eats place, where credit cards won’t be accepted. Street festivals and fairs are also good examples of places that need cash.

Will my bag be checked?

If you will visit large venues, like stadiums, ballparks, concerts, museums, festivals, and theaters, you will have to show the inside of your handbag for security purposes. Some large items might not be permitted or held for you, so know the rules of the places you want to visit in advance.

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What are the best places to stay at?

To enjoy the spirit of Chicago, skip the chain hotels and stay at Chicago Athletic Association, Ace Hotel, Freehand, Hotel Lincoln, and The Robey. Or you can do even better – rent somebody’s apartment or house from Airbnb or Home Away.

Should you take a tour?

Absolutely! River boat tours are amazing and popular even among locals. There are also plenty of walking, biking, and even Segway tours to see more of the city. Food and beer tours are perfect for all food connoisseurs.

What shoes should you bring?

You can bring any shoes you want, but may we advise against high heels? You will be walking a lot from point to point, even between rail stations, so wear something comfortable and weather appropriate.

What about clothing?

Chicago is called Windy City for a reason. Summer days can be interrupted by summer storms any time and the rest of the year that wind from Lake Michigan can really dampen your spirits. To avoid all that, wear lots of layers, always.

When is the best time for a visit?

Chicago is beautiful any time of the year, but summer is definitely the busiest time with good weather, outdoor dining, rooftop bars, parks, Cubs and White Sox games, beaches, and lake tours.

What areas of Chicago should you see?

If you want to see the real Chicago, you should definitely get out of downtown and venture into neighborhoods for unique cuisine and local spirit.

United State Maps With Cities

What museums should you see?

Chicago is rich with museums and you can spend a week just on that easily, but if you don’t have a week to dedicate to museums, visit at least the Art Institute and don’t expect to see it all in one afternoon either. Illinois residents can visit some museums for free on designated free days, and the rest of us can benefit from City Pass discounts.


If you happen to be Chase Private Client, this is what you can get free:

  • - Adler Planetarium – free for you and 2 guests, 20% off membership, 50% off sky shows, 10% discount at stores
  • - Art Institute of Chicago – free admission and 10% off dining
  • - Chicago Children’s Museum – free admission for you and 1 guest, 10% off gift shop
  • - Field Museum of Natural History – 2 free tickets, discounted special exhibitions
  • - Museum of Science and Industry – 2 free tickets

Are there tours of street art?

The best way to see street art is to walk everywhere and see things for yourself. For example, there is an unnamed Picasso sculpture in Daley Plaza, “The Bean”, Murals by Hebru Brantley and Kerry James Marshall, mosaics by Marc Chagall, sculptures by Lorado Taft, and future video art on Merchandise Mart façade.

How late can you find a party in Chicago?

Chicago likes to party and most of the bars and clubs in the city are open until 2 am, 3 am on Saturdays. After that there are some bars that can pour you a drink until 4 am on weekdays and 5 am on Saturdays. The most serious party people can always grab a bite at 24-hour restaurants.

Where is the best shopping in Chicago?

As we said before, skip the Magnificent Mile with its boring retail and go to Wicker Park, Bucktown, Lincoln Park, Lakeview, and Andersonville neighborhoods.

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