Planning A Trip to Chicago in Summer: 8 Must-See Attractions & Travel Tips

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Planning a trip to Chicago in summer is a great adventure, especially when you know what the must-see attractions are. You can book a stay in a Chicago hotel, ranch, house, or condo to take advantage of the beautiful sunny season. Simply follow these travel tips and you will thoroughly enjoy visiting the “Windy City.”

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Editor’s Note: This article was updated in April of 2022.

CONTENTS – In this article, you will learn how to prepare for a special summer trip to Chicago, plus the 8 best places to visit:

Travel Tips for Chicago – Preparing For A Special Summer Getaway

After months of isolation during the pandemic, it’s time for Chicago to celebrate the end of quarantine. As a result, the city is pulling out all stops that will offer entertainment, dining, and drinks at venues throughout the downtown area.

If you are planning for a summer getaway to Chicago, several exciting events are coming up that will be perfect for you and your loved ones. 

But before you jump and participate in these activities, you need to plan your stay and book a vacation rental; contact your Chicago injury lawyer to make sure you are covered. Besides, there’s no better way to spend your vacation than with the assurance that you are protected.

To make the most of your summer adventure this year, here’s what you need to prepare for a solar trip of a visit with the whole family.

Best Time to Visit Chicago

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While this may seem like a no-brainer, it’s essential to prepare for the weather conditions and make sure you have everything with you when you visit Chicago.

In terms of Chicago weather, it’s known as “the windy city” because it is naturally breezy on the shores of Lake Michigan. In fact, wind speeds in severe storms can reach over 200 MPH and Chicago has recorded some of the most extreme weather in the US.

It gets really cold in the winter time, too, with an average low of 14.3°F on winter nights in January, with days barely above freezing.

Some say the best months to visit Chicago are in the spring (April, May) or fall (September, October), when the temperatures are mild and you’ll find fewer crowds.

But if you’re visiting Chicago in July, don’t worry! You’ll enjoy an average high of 83.5°F and a low of and low of 70°F, which is perfect vacation weather. Summer in is a great time to visit Chicago!

Expect to see some rain in July and August, so you’ll want to bring along an umbrella or raincoat just in case it rains during your stay. That’s especially important if you have events planned outside your vacation rental property in Chicago.

Getting To Chicago

There’s many ways to get to Chicago: taking a road trip, traveling by bus, planning a trip to Chicago by train, or flying to Chicago. Most visitors from afar to Chicago fly in.

The two airports in Chicago are O’Hare International Airport (ORD) and Midway International Airport (MDW). As you might know, O’Hare is one of the busiest airports in the world. The good thing is, you’ll likely find a good flight from your city. If you’d like to avoid the big airport, opt for Midway.

If you are a frequent flyer, you may even want to consider fractional private jet ownership. By investing in a share of an aircraft, you’re afforded a certain number of flying hours and taxi time.

Depending on where you live, you can easily get to Chicago by train, car, or bus, too.

Several major interstates and highways are convenient to Chicago, including  I-90, I-94, I-55, I-290, and I-294. Note that some, like the Tri-State Tollway (I-294) will require you to pay tolls along the way. (You’ll also want to do some research on parking options downtown.)

If you prefer to sit back and enjoy the ride on public transportation, both Amtrak rail service and Metra commuter trains arrive into Chicago’s famous Union Station. Charter busses, Greyhound, and the budget-friendly Megabus also serve the city.

Related: How to find a good flight.

How to Get Around Chicago | Travel Options

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Once you get there, you’ll want to figure out your transportation options for getting around and about in Chicago. 

If you are driving your own car or a rental car, it’s crucial to have a map. Even though you will likely have GPS on your smartphone or vehicle, you want to get a visual lay of the land before hand you so you have a better sense of where you’re going.

No worries if you won’t have a car. It’s easy to navigate Chicago without one. You can rely on travel by bus or public transportation, so have a look at routes and schedules of the Chicago Transit Authority and Metra Commuter Rail. You can pretty much get anywhere in the city that way.

Even though CTA’s “L” has had some bad press in the past, you’ll feel safer in Chicago knowing they’ve invested $26 million dollars to expand the transit, which includes 3,600 cameras on rail cars and platforms.  

You can also Uber (or Lyft), taxi, or bicycle around Chicago with ease. 

It will also be helpful to know the location of public restrooms and parking spaces near your vacation activities, rental property or hotel in Chicago.


Regardless of your travels, it’s imperative that you drink lots of water during the summertime. When you’re vacationing though, it’s even more important. 

That’s because you’ll be sightseeing, on the go, and may be more active than your normal routine–so you may not even think of it. You probably won’t even get thirsty.

Even so, make sure you carry a refillable bottle with you at all times, especially if you’ve planned a lot of outdoor activities for your trip to Chicago. The body needs hydration for optimal performance and you don’t want to tour the hospital on any vacation.

Healthy Snacks

It doesn’t matter if your Chicago vacation includes the Shedd Aquarium or a fun day at Navy Pier, be sure to eat healthy throughout your stay to avoid getting sick from summer excitement. 

Sure, you’ll probably want to eat at some of Chicago’s better restaurants, and try that famous Chicago deep dish pizza, but don’t arrive famished. 

Instead, pack some granola bars, fruit, and nuts for snacks along with your bottled water. You can just keep them in your backpack so you have them handy when you feel your energy levels drop. 

Related Article: Here are more summer safety tips you should know.

Dress for Comfort

While traveling to Chicago, wear your most comfortable shoes and clothes. Go for outfits that can transition easily from day to evening activities.

You don’t want anything too loose or tight that will prevent you from enjoying the summer festivities planned for your trip. The last thing you need is a wardrobe malfunction during one of those fun activities!

Top 8 Places To Visit In Chicago in the Summer

Once you’re ready to make your way to Chicago, here are some great things to do in Chicago this summer. They’re the “must-see” attractions in Chicago while staying in the city during summertime – or anytime for that matter.

1. Shedd Aquarium

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The Shedd Aquarium is a family-friendly oasis with fun activities for all ages and animals from around the world! This is a wonderful take even if you don’t have kids in tow. Plus, there’s an IMAX theater where you can watch movies about marine life.

2. Chicago Botanical Garden

Visit the Chicago Botanical Garden to see rare plants, take a walk through nature trails, or visit the onsite cafe. You’ll also discover a spectacular indoor conservatory that is filled with tropical flowers year-round!

3. Navy Pier

The multi-purpose Navy Pier offers attractions for all age groups, including children, where you can enjoy carnival games, visit an IMAX theater, or enjoy a boat ride. It’s an indoor, temperature-controlled experience with light sculptures (60,000 lights!), an indoor rink, a beer garden, and more. It’s very affordable, too!

4. Millennium Park

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Millennium Park features several attractions, including Cloud Gate (also known as “The Bean”), Crown Fountain, and Lurie Garden. This park will keep you entertained for hours! While you’re there, be sure to visit the Jay Pritzker Pavilion where live performances take place.

5. Field Museum of Natural History

There’s so much to see inside the Field Museum of Natural History, including dinosaur fossils, ancient artifacts, and mummies – specifically, 4.5 billion years of history!

When you’re planning a trip to Chicago, be sure the Field Museum of Natural History is on your itinerary.

6. Lincoln Park Zoo 

Lincoln Park Zoo is full of fun activities for children, like feeding animals at Lakeside Cafe or observing penguins dive underwater through the glass tunnel. 

In Lincoln Park Zoo’s specially designed animal exhibits, you’ll encounter nearly 200 unique species from around the world, including endangered and thought-to-be-extinct animals. The gardens also feature more than 2,000 plant species. 

Heck, this is fun for anyone who loves seeing nature up close!

7. Wrigley Field

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You can watch a baseball game at the home field of the Chicago Cubs, one of two Major League Baseball (MLB) teams in Chicago. (The other is the White Sox.) Wrigley Field is on the north side of Chicago in a primarily residential neighborhood. 

8. Chicago Bulls and United Center

If basketball is more your thing, then you can cheer on your team at the Chicago Bulls | United Center in one of their games, which draws sports fans from all over.

Final Thoughts on Summer in Chicago

The summertime is a great time to travel with friends, family, solo, or with that special someone. Whether you’re planning a trip to Chicago that’s just for a week or two weeks, Chicago hosts plenty of activities and festivals throughout different seasons each year. 

Make sure you take along the items mentioned above to ensure that your vacation in Chicago is a fun-filled stay. 

So. is Chicago worth visiting? It doesn’t matter if you’re a frequent Chicago visitor or If you’re visiting Chicago for the first time, we think you’re gonna love it.

To continue reading, click through to these 9 useful travel tips for Chicago next.