Plan Your Chicago Trip

How to Plan Your Chicago Trip

Planning a trip to Chicago is very easy if you plan it properly. At the same time, planning your Chicago trip can be hard without knowing the starting point.

Nothing to worry, this post will help you plan a trip to Chicago that fits your budget and preferences. On this page, you would find all necessary information and links to my guide that will help you plan a trip to Chicago.

Being one of the major cities in United States of America, it is very easy to get to Chicago by air. Chicago city has two major airports – O’Hare International and Midway airport.

You can also get to Chicago by train or by bus, but I recommend you to go by air to save time. If you live in neighboring states then I recommend you to drive your car over flights, unless you find a cheap airfare to Chicago.

For booking a flight to Chicago, I recommend well-known companies such as Travelocity, Priceline or Expedia. Make sure to check their Chicago vacation package deals to save even more when you book Flight + Hotel together.

I recommend Expedia.com for booking a Chicago hotel for less. Try to book flight and hotel together to save more money.

Book Chicago Hotels for Less

Also, when planning your trip to Chicago, you must book your hotel as early as possible. Especially if you are traveling during peak season – June, July and August months. If you find any good hotel room deals then it is very likely to get sold out quickly.

If you find a good hotel deal during peak season then I recommend you to book hotel room immediately. You can read my where to stay in Chicago post to get more idea while booking a hotel room.

You can check hotel deals on Booking.com, Expedia.com or Hotels.com to get the best rates.

I recommend you to adjust your travel dates to avoid any major conventions in Chicago. Try to avoid major conventions to get lower rates on hotels as hotel room rates will be very high.

It is always a good idea to catch one of shows or concerts 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.

You can read my When to Go to Chicago post to get more information about best time to visit Chicago.

You must check weather before packing your bags for your trip to Chicago. Weather in Chicago is very unpredictable so it is always good to check weather a day before your travel dates before packing your bags.

International Travelers require USA visa to visit Chicago. If your country of citizenship falls under the Visa Waiver Program (VWP), then you can enter the United States without a visa that will allow you to stay for 3 months.

Whether you are US Citizen or International visitor, you may bring in pre-defined size of alcohol and tobacco products. You are allowed to bring in cigarettes and cigars, but there are some restriction on cigars from Cuba. You can get detailed information on US custom website.

I recommend you to utilize public transportation in Chicago to save time and money. Both O’Hare and Midway airports are connected with downtown through EL trains. O’Hare is on Blue line El trains and Midway is on Orange Line El trains. You may like my post on getting around in Chicago.

If you are planning to travel through trains and buses then I recommend you to purchase CTA Visitor Pass. It allows you to take unlimited train and bus rides for a 24-hour period. It will save your lot of money.

CTA Visitor Passes are sold at airports, transportation hubs or tourism information center. You can also purchase them in advance online at transitchicago.com.

Chicago city has total seven different EL train lines, out of all you will probably need “The Red Line” in downtown Chicago as it runs parallel to the Michigan lake, along several top Chicago attractions.

I also recommend tourists to take Brown Line which runs around the downtown Chicago loop.

I highly recommend you to take at least one EL train ride to get the different experience in Chicago, passing through downtown buildings and residential areas.

Senior traveler above 60 years of age can get discounted rates on admission to participating hotels, attractions and theaters. Also senior residents of Chicago can travel for free on local public transportation with valid proof.

Chicago Trip Planner Guide

• When to Go to Chicago – Advice on best time to visit Chicago.
• Getting to Chicago – Advice on getting to Chicago
• Getting Around Chicago – How to get around Chicago for tourists
• Airport Transportation – Best way to/from Chicago airports.
• Weather in Chicago – What is weather like in Chicago?
• What to Pack for Chicago Trip – Packing tips for Chicago trip.
• Traveler’s Helpline – Ask and give advice to fellow Chicago travelers.

Where to Stay in Chicago

Where should you stay in Chicago? It’s challenging and more confusing while planning a Chicago trip or even for a local getaway to unwind and relax in hotel away from daily routine life. Chicago is one of the largest metro city in USA. Chicago city covers large radius of area, that offers plenty of hotel rooms to stay, and more options creates more confusions.

If you are not familiar with Chicago then it might get pretty confusing when it comes to booking a hotel room to stay during your trip. You can find more information before booking a hotel room in my where to stay in Chicago post.

• Where to Stay – My recommendations on booking a hotel room in Chicago!
• Chicago Downtown Hotels – Get deals on downtown hotels.
• Chicago Pet-friendly Hotels – Check out pet-friendly hotels in Chicago before you plan your trip with your furry friend.
• Chicago Luxurious Hotels – Plan a luxurious getaway in Chicago.
• Chicago 5-Star Hotels – List of 5-star hotels in Chicago.
• Chicago 4-Star Hotels – List of 4-star hotels in Chicago. Most likely you will be booking one of these hotels.
• Chicago 3-Star Hotels – List of budget-friendly hotels in Chicago.
• Chicago Hostels – Get advice on hostels in Chicago.
• How to Compare Chicago Hotels
• How to Find a Hotel Room in Chicago

What to Do in Chicago

There are plenty of things to see and do in Chicago. Most of all top attractions are located in and around the downtown Chicago, including Willis Tower, Navy Pier, the Field Museum of Natural History, the Shedd Aquarium, the Millennium Park and Magnificent Mile.

I highly recommend you to use one of the Chicago attraction passes to save money on admission to attractions. I would suggest you to use either Go Chicago Card or Chicago CityPass based on your number of days on hand to explore the windy city.

• Family Friendly – Best family friendly Chicago attractions.
• Kids Friendly Chicago – List of kids friendly Chicago attractions.
• Chicago Museums – Plan which museum fits your taste.
• Zoos & Aquariums – List of zoos and aquariums in Chicago.
• Chicago Shows – Famous Chicago shows and more

Chicago Tours

Chicago city offers many tours such as Chicago food tours, boat tours on lake and Chicago river, bus tours, walking tours, Segway tours and many more. I recommend you to book tour tickets online at Viator.com in advance before visiting Chicago.

If you are planning to buy Go Chicago Card to explore Chicago then check before purchasing tour tickets separately as some of these tours are already included in all-inclusive Go Chicago card.

• Chicago Boat Tours – Ways to sail on Chicago river and Michigan lake.
• Chicago Bus Tours – Go see Chicago with your guides on wheels.
• Chicago Food Tours – Eat and have fun in Chicago.
• Chicago Segway Tours – See Chicago without walking.
• Chicago Day Cruises – Sail Michigan Lake to enjoy excellent skyline views.
• Chicago Night Cruises – Great way to enjoy Chicago Skyline at night time.

Chicago Itineraries

I have come up with some sample Chicago Itineraries that may help you plan your visit to Chicago. I would recommend you to create your Chicago Itinerary using popular Chicago attraction passes, Go Chicago Card or Chicago CityPass, to save lot of money on admission tickets to attractions.

• One Day Chicago Itinerary – Explore Top Attractions on Budget with Go Chicago Card
• Chicago 1-Day Itinerary – Plan a trip to Chicago with sample one day itinerary for Chicago.
• Chicago 2-Days Itinerary – Plan a trip to Chicago with sample second day itinerary for Chicago.
• Chicago 3-Days Itinerary – Plan a trip to Chicago with sample third day itinerary for Chicago.
• Chicago 4-Days Itinerary – Plan a trip to Chicago with sample fourth day itinerary for Chicago.

Plan a Trip to Chicago with Maps

• CTA – CTA Bus and Rail lines, as well as connecting services in Chicago
• Metra – Travel to Chicago suburbs.
• Bike – Plan your bike path before you start.

Where to Eat in Chicago

• Best Chicago Restaurants – List of top Chicago restaurants that fits your taste buds.
• Best Waterfront Bars – Advice to enjoy the waterfront bars in Chicago.

How to Book Chicago Trip

• Find Chicago Vacation Packages – Book Flight + Hotel together and save up to $525 per person.
• Find Chicago Hotel Rooms
• Find Flights to Chicago
• Car Rentals in Chicago
• Go Chicago Card – Save 55% on admission to Chicago attractions.
• Chicago CityPass – Save 50% on VIP admission to the 5 best attractions in Chicago.
• Book Chicago Activities – If Chicago attraction passes are too much for you then book specific activity in Chicago.