Planning Your Vacation to the Windy City

How To Plan Your Vacation To The Windy City

The votes are in, and the Windy City won as your next vacation spot. But, with so many world-famous museums, amazing architecture and endless entertainment and dining options, planning your trip to Chicago can be a bit overwhelming. Lucky for you, we know a thing or two about the city. Watch your Chicago travel plans fall into place with the help of our travel guide.

When to Go

Chicago is a great destination year-round, but it’s important to note the differences among the seasons. Summer is the prime visiting time, so expect crowds and hot temperatures. The advantage to summer is the festivals, special events and outdoor activities. Fall offers a reprieve from the soaring temperatures, and there are fewer visitors. Chicago winters are notorious, but they aren’t all bad. The city sees plenty of snow and the temperatures dip low, but winter is not nearly as busy, and you’ll save money on hotel rooms. Chicago also offers some amazing holiday events. Spring is often unpredictable. You may enjoy sunny, warm weather, or you may find yourself in the middle of a snowstorm.

Planning Your Itinerary

You can do the highlights version of Chicago in a weekend, but planning a trip of at least five days lets you really experience what the city has to offer. Even when you can spend several days in the city, planning an itinerary is a good idea to ensure you see everything you want to see.

Planning a trip of at least 5 days lets you really experience what Chicago has to offer.

Start by deciding on the length of your trip, including the dates of travel to help you narrow down events that occur on certain days. If you won’t arrive until midday or evening, leave your arrival date open without any scheduled activities, so you have a chance to settle in and soak in the vibe of the city.

No matter how large or small your travel group, use these tips to determine which Chicago hotspots make your itinerary:

  • Brainstorm a list: Before narrowing down the options, make a list of all the Chicago destinations that interest you and your travel party. You can always cross things off if you don’t have time. A list will generate plenty of ideas to get the planning started.
  • Let everyone choose one: Unless you have a huge party that makes it impossible, let each person choose one must-do activity. Everyone should have a say — it will ensure everyone in your travel party feels valued.
  • Set a tone: What is your goal for the trip? Do you want to be relaxed and spontaneous? Do you want to delve into the nightlife? Are you determined to visit as many museums as possible? Do you want to stay active while you explore Chicago? Deciding on the overall feel of the trip helps you plan an itinerary that meets those goals.
  • Be realistic: Don’t try to pack too much into one day. If your schedule is packed from morning to night, you may find yourself rushing and missing some amazing things. Stick to one or two major activities each day with some filler activities if time allows.
  • Account for travel time: Consider travel time to navigate around the city. Chicago is expansive, and it takes some time to travel from one point to another. If you’re relying on public transportation, you may have to wait for the train or bus.

Where to Stay

Chicago offers a wide range of hotels from upscale boutique hotels near the Loop to inexpensive chain hotels near the airports. You can find great hotels in most parts of the city, but certain factors help you narrow down your search. Consider these factors when choosing your hotel location:

  • Itinerary: Are most of the activities on your itinerary in a particular part of the city, or are you in the city for one main reason? Choose a hotel close to the action for easier access and lower transportation costs.
  • Budget: You can spend hundreds of dollars a night on some hotel rooms, so having a general budget in mind helps you narrow down your options.
  • Amenities: Check out the amenities for each hotel to determine if they fit your needs. For example, finding a pool in a hotel downtown is a little more difficult.
  • Parking: If you’re staying in downtown Chicago, expect to pay for parking at your hotel. Check out the security and the costs associated with parking.
  • Access to transportation: You’ll likely use some form of public transportation while in Chicago. Find a hotel close to your preferred mode of transportation for ease of access.

Staying in the suburbs is also an option, but you need to account for more travel time each time you head downtown for activities. If you’re feeling more adventurous, check out other options like hostels, Air BnB, or even Bed & Breakfasts.

Getting Here

Chicago offers access via air with two airports: Midway and O’Hare. Flying into Chicago instead of driving saves you the headache of navigating toll roads and the seemingly endless interstates zigzagging through the city. By the way, Chicago interstates are numbered, but they are more commonly known by their expressway nicknames, such as the Eisenhower or the Kennedy. Keep this in mind if you receive directions from a local.

The option of flying into two different airports gives you more flexibility on fares. Check the cost to fly into both. O’Hare is larger, but you may find reasonable flights to Midway as well. Even if you are within driving distance of Chicago, flying can be more convenient. You can take the L from either airport to downtown Chicago, and you don’t have to drive through the city or pay for parking.

Another option to get to Chicago from certain cities is the Megabus. The express bus service runs between Chicago and several U.S. cities, including Dallas/Ft. Worth, Ann Arbor, Des Moines, Minneapolis, Nashville and Detroit among others. Fares are relatively low, and you leave the driving to someone else.

Driving can be an affordable way to head to Chicago if you live in the Midwest. As long as you’re prepared for the traffic and have a good navigation system, you can get yourself where you need to go. Budget for tolls depending on your route into the city and parking costs at your hotel if you stay downtown.

Getting Around Chi-Town Once You’re Here

If you drive to Chicago, you probably won’t need your vehicle once you arrive. Chicago offers a robust public transportation system that is often faster than driving yourself. Parking is even worse than trying to navigate the city streets. It’s tough to find a spot anywhere in downtown Chicago. Save yourself the trouble by taking advantage of public transportation.

Getting Around Chicago Is Easy With Options Like The L, Buses, and Walking!

Some options for getting around the city include:

  • The L: The elevated train can get you almost anywhere in the city. With frequent stops, you can get fairly close to most places you want to go in Chicago.
  • Buses: Chicago also offers a bus system to get around town. Just like the train, bus stops are frequent, meaning you can get where you want easily with just a short walk from the bus stop.
  • Taxis & Ride Shares: If you prefer a direct route without sharing a ride with hundreds of other people, grab a taxi or use a ride sharing service to get to your destinations each day. Chicago has plenty of cabs to help you get around.
  • Free trolley: Chicago offers three free trolleys with limited service to Navy Pier and Randolph Street Market. While this is a fun way to get around, the wait can be quite long. You may prefer to pay a little for other forms of public transportation rather than spend a long chunk of your day waiting for the trolley.
  • Walking: When you stay close to the action, walking is one of the best ways to get around the city. You eliminate the wait for public transportation, and you get to see the city up close. Make sure you know how far away your destination is before you start walking to ensure you can handle the distance.

Things to Do in Chicago

Chicago has no shortage of activities to consider, including museums, theater, outdoor activities, sporting events and festivals. Some activities are quick and easy, while others deserve a little more time to explore. When you plan a longer trip to the city, you have more time to explore the attractions that require more time.

Some of the more involved activities include:

  • Lincoln Park Zoo: You could buzz through the Lincoln Park Zoo quickly, but we suggest taking your time to soak in the park-like feel of the free zoo. Wander as much as you want without paying a dime.
  • Museum of Science and Industry: The museum has a number of amazing exhibits, including a replica of a coal mine, the U-505 submarine and tons of interactive exhibits. You should dedicate several hours to visiting the Museum of Science and Industry.
  • Field Museum: Sue the T-rex is a big draw at the Field Museum, but you can find plenty of other interesting exhibits to keep you entertained for hours.
  • Art Institute of Chicago: Whether you’re an art lover or not, this museum gives you access to amazing artwork. You can easily spend several hours there if you enjoy art.
  • Shedd Aquarium: The aquarium is a popular tourist spot, which means long lines and crowds. Expect to spend a while here exploring the different exhibits and fighting the crowds.

We suggest taking your time to soak in the park-life feel of the free zoo.

Other activities that can take as little or as much time as possible include:


  • Millennium Park: You’ve no doubt seen plenty of photos taken in front of the Bean sculpture, which is officially called Cloud Gate. You can take your own selfie there when you stop at Millennium Park — a great place to stretch your legs between other activities in the area.
  • Willis Tower: Chicagoans will always call it Sears Tower, but whatever you call it, the observation deck is a must. It gives you an amazing view from high above the city.
  • Wrigley Field: You don’t have to travel to Chicago during baseball season to visit Wrigley Field. The stadium host tours with various options.
  • Navy Pier: No trip to Chicago is complete without a stop at Navy Pier. Inside, you’ll find the Chicago Children’s Museum, an IMAX theater, many dining options and an amusement area complete with a Ferris wheel, swing ride and mini golf.
  • Chicago Riverwalk: Stroll along the river to see a variety of architecture. Public walkways give you access to the riverfront views.
  • Adler Planetarium: This is the place to learn about everything astronomy. In addition to all of the telescopes and astronomy information, Adler offers some amazing views of the city and the lake.
  • Breweries: Chicago serves as home to many locally owned craft breweries, many of which offer tours and tastings.
  • Second City: Chicago has many comedy clubs, but Second City is one of the best known. Take in a show or visit another club for a comedic break.
  • Architectural cruise: You’ll find many cruise options in the city, all of which give you a view of the city skyline from the water. The length of time varies, but many of the cruises last between 1 to 2 hours.
  • Festivals: You can find various festivals almost every weekend throughout the summer months. The festivals celebrate everything from food trucks and craft beer to art and local culture. You can even find special events and festivals in the winter months, although you’ll want a warm parka if the event involves any length of time outdoors.
  • Theater: Chicago offers a varied theater scene, from small local theaters to professional productions. Find tickets to the productions that fit your interests.

Easy Day Trips From Chicago

If you want a break from the city, there are many easy day trip options that let you explore the Midwest a little more. Rent a car, and take off to explore the surrounding area with one of these day trip ideas:

  • Milwaukee, Wisconsin: If you want to experience another Midwestern city, head north to Milwaukee. The city offers a variety of cultural events and plenty of lakefront views.
  • Lake Geneva, Wisconsin: About 80 miles northwest of the city, you’ll find the historic town of Lake Geneva with plenty of independently owned restaurants and shops to keep you busy. The area is also full of activities such as zip lining, horseback riding and golf.
  • Indiana Dunes National Lakeshore: Head 50 miles southeast to find Indiana Dunes National Lakeshore and State Park, with woodlands, sand dunes and wetlands. The area includes 15 miles of beaches and 50 miles of trails, perfect for active tourists who want to connect with nature.
  • Rockford, Illinois: Just 90 mile west of Chicago lies Rockford, a city known for its growing foodie scene, public gardens and cultural attractions.
  • Evanston, Illinois: A little closer to the Loop, Evanston is only about 15 miles north of Chicago, but it offers a completely different experience. Visit the lighthouse or wander the Northwestern University campus.

Indiana Dunes National Lakeshore has 15 miles of beaches and 50 miles of trails.

Tips for a Successful Trip

With your basic itinerary in place and reservations made, you’re almost ready to vacation in the Windy City. Before heading out, consider these extra tips to make your trip a success:

  • Buy tickets online: Buy your tickets online ahead of time. Most of the museums and other major attractions offer this option. You often save a little money, and you can skip long lines when you arrive.
  • Use CityPASS: Another option to save time is the CityPASS, which provides you with VIP access to Shedd Aquarium, Skydeck Chicago, the Field Museum, the Museum of Science and Industry and Adler Planetarium. You can skip lines, and the cost of the CityPASS saves you significantly over cost of individual tickets to the included attractions.
  • Use Go Chicago Card: This card is similar to CityPASS, with entry to various attractions at a discounted rate. The Go Chicago Card offers an option to customize the experience by choosing the attractions you want to visit.
  • Plan ahead: You don’t need to schedule every minute of your trip, but a general itinerary allows you to get the most out of the trip.
  • Stay flexible: Even with your itinerary in hand, things can change on a whim. Keep some flexibility in your schedule, so you can enjoy the city.

Now that you know more about traveling to Chicago, what are you waiting for? Start planning your trip to ensure you hit all the must-do attractions on your itinerary. While you’re here, experience Chicago pizza at its finest at one of our Giordano’s locations.