Chicago Insider Travel Tips : You Must Know From A Local

Chicago is one of the major cities in USA, and every year millions of visitors travel to Chicago for leisure and business.

Our windy city has lot more to offer then we can imaging from public transportation systems to world famous museums, landmarks, architecture and activities.

But, so many options always creates confusions. Yes, very minor looking matters might make a big difference while planning your trip to Chicago.

Today I decided to come up with certain Chicago insider travel tips that might look minor but they can be beneficial for both Chicagoans and visitors.

I recommend you to consider following facts while planning a trip to Chicago. I admit that I didn’t know many basic things about our city until I started to explore.

Sometimes I get surprised after knowing the money saving facts while getting around in Chicago using public transportation, visiting attractions, eating out and many similar.

This list of few Chicago insider travel tips can be useful for Chicago visitors or Chicago locals anytime of the year.

I plan on keep updating the list of my Chicago insider travel tips regularly, whenever I come across something that can be useful to explore Chicago.

Chicago Insider Travel Tips

First and most Important – Be Friendly!

We Chicagoans are very friendly people. I suggest you to try to be friendly when you go to restaurants, cafe, shops, bars or any attractions. Do not hesitate to say hello! It’s our Midwest lifestyle.

We do not like to slam doors on faces. Yes, don’t forget to hold the door for people behind you. It’s true, you will be surprised to see that even 80 plus years older senior person holding a door for you.

Book Your Hotel Early

When planning your trip to Chicago, always book your hotel in advance. If you find a hotel deals in Chicago that fits your budget then do not wait too long as best rate hotel rooms will sell out quickly.

Summer is peak season in Chicago among tourists – maximum numbers of tourists visit Chicago during June, July and August.

If you find a good hotel room deal in Chicago for those months then you must book that hotel immediately.

Do not wait longer otherwise those rooms might get sold out pretty quickly during peak season.

You can find best hotel deals from big travel companies like Booking.com, Expedia.com, Hotels.com and Travelocity.com. You might be able to get the cheapest hotel deals on Priceline through name your own price auction.

Adjust your travel dates to avoid any major conventions in town. During major conventions, hotel room rates will be very high.

Packing for your Chicago Trip

You must check a day before your travel dates before packing your bags. Chicago is known for weather, we always joke that if you do not like weather then wait for an hour and it will change.

Navigating Chicago: Public Transportation

Walking is the best way to explore Chicago downtown. But if you are traveling longer distance then I recommend you to use public transportation in Chicago. City offers great public bus and train systems.

I must warn you to avoid taxi, UBER or Lyft during rush hour to get to the downtown Chicago. If you do not have heavy luggage then you must utilize public transportation.

O’Hare International airport is on CTA Blue Line “EL” train and Midway airport is on CTA Orange Line.

I would not recommend you to go for EL train option, if you are traveling with heavy luggage. You will have a good amount of walking to get to the EL station at both airports. In that situation, UBER or Taxi is the only best option to get to downtown Chicago or hotel.

If you are planning to travel through city by trains and buses then consider buying a Visitor Pass. This Visitor Pass allows you to take unlimited numbers of train and bus rides over next 24 hours.

CTA Visitor Pass you can purchase at airports, transportation centers or at Chicago’s Tourist information center. Some hotels in Chicago also sell CTA Visitor Passes. You can also purchase it online at transitchicago.com

FREE rides in downtown Chicago

City of Chicago runs free trolley between Michigan Ave and Museum Campus. If you are planning to visit Adler Planetarium, the Field Museum of Natural History and/or the Shedd Aquarium then you may take advantage of these free trolley in downtown Chicago.

These free trolley operates everyday during summer season, but during fall and spring seasons they are available during weekends only.

I was surprised to know that these free trolleys operates year round between Navy Pier and the Red Line El station on the Grand/State street.

Use Chicago Attraction Passes to Save Money

You must use one of the available attraction passes in Chicago. It is not joke, you will be able to save lot of money on admission tickets to attraction.

Currently, there are two most popular attraction passes in Chicago. I have used and recommend Go Chicago Card and Chicago CityPass to explore Chicago’s top attraction on budget.

You may also like my post on free things to do in Chicago in summer and top things to do in Winter in Chicago.

Must Experience Chicago Architecture Cruise

I insist, you must experience Chicago’s Architecture guided tour. There are many companies offering architecture cruises on Chicago River and Lake Michigan. I have used Wendella tours and Shoreline Sightseeing Tours.

Book Show Tickets Before You Arrive

There are many shows and concerts to attend year round in Chicago. It is always a good idea to catch one of those shows in Chicago during your visit.

You must book your show tickets online before you arrive in Chicago. I recommend you to check out Ticketmaster or theater website to book show tickets online.

Deep Dish Pizza

Chicago is known for deep dish pizza. My favorite deep dish pizza places are Lou Malnati’s and Giordano’s. It’s strange but majority of Chicagoans do not eat deep dish pizza all the time, except we have to entertain guests in town. 🙂

You may like my post on Chicago style food you can order online.

Photo Perfect Spots

There are many photo perfect spots in Chicago, but I would recommend you to try lake front beach, The Cloud Gate so called “The Metal Bean”, and roof top bars like London House and Cindy’s.

Must Explore Chicago Neighborhoods

Chicago downtown is popular among tourists as majority of top attractions are located around the loop. But, you must plan on visiting Chicago’s neighborhoods to experience the unique vibe.

My favorite neighborhoods are Wicker Park, Lake View, Lincoln Park, Old Town, Gold Coast, Logan Square, West Loop and Avondale. Chicagoans must experience all neighborhoods but I would recommend tourists to visit at least few from my favorite Chicago neighborhood list.

More Chicago insider travel tips to come as I keep exploring Chicago. Keep above tips while planning a visit to Chicago and you will save time and money during your trip. Stay tuned to get more updates on Chicago insider travel tips!

Comments

comments