A Complete Guide for a Chicago Road Trip

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Packing for a Chicago road trip is a great way to explore the metropolis, scout the neighborhoods, soak in the breathtaking views, and create memorable experiences. 

If you’re planning a road trip to Chicago, the Windy City, it’s essential to be well-prepared to make the most of your adventure. 

Since I have lived and driven in the Chicago area for over 30 years, you can use this guide that I created to help you through the essential items to pack, tips for driving in Chicago, road safety tips, and more. 

So, fasten your seatbelts and get ready for an exciting journey!

Essential Items for a Chicago Road Trip

Firstly, let’s get the obvious items out of the way. Although they apply to just about any road trip, I think it’s important to keep this in mind for Chicago too.  

  • Comfortable Clothing: When starting your road trip, opt for comfortable clothes that are suitable for long hours of sitting. Choose breathable fabrics, such as cotton, and consider layering to adapt to changing temperatures during your road adventure.
  • Weather-appropriate Gear: Depending on the time of year, Chicago’s weather can be unpredictable, so pack accordingly. In spring and fall, you will want to layer your clothing. Bring a light jacket or sweater, a raincoat or umbrella, and hats and gloves for colder seasons.
  • Snacks and Drinks: Keep yourself fueled during the drive with a variety of snacks like granola bars, fruits, nuts, and bottled water. During summer, bring a cooler for the trip to stay hydrated and to store perishable items. It will also save you time and money so that you don’t have to stop and spend extra dollars at pricey convenience stores. 
  • Navigation Tools: Ensure a smooth journey by bringing a GPS device or using a reliable navigation app on your smartphone. For your road trip, you could have a physical map or printed directions that serve as backup.
  • Entertainment Options: Long road trips can be tiresome, so pack entertainment options like books, podcasts, or audiobooks. Prepare playlists with your favorite music to keep the atmosphere lively. Also, pack some games and movies or have a list of engaging car games prepared for the little ones when traveling on a road trip. 
  • Roadside Emergency Kit: Prepare for unexpected situations by carrying a roadside kit. It’s always wise to be prepared for any emergencies on the road. Put together a roadside emergency kit that includes a spare tire, jack, jumper cables, flashlight, first aid kit, basic tools, and a roadside assistance contact number. Additionally, consider adding a portable phone charger and extra batteries to stay connected.

Tips for Driving in Chicago

When it comes to driving in Chicago, there are a few things that people might not know. First and foremost, be prepared for the notorious traffic congestion, especially during peak hours.

Chicago has a public transportation system. I advise that you use it as much as possible because it will save you time and money especially during peak season, while visiting the city.

Peak Traffic Hours

The morning peak hours going into Chicago are between 6 AM and 9 AM. The peak hours leaving Chicago are between 3 PM and 7 PM.

The evening hours extend just a bit because some like to visit happy hour events, so the peak period is a tad longer.

Anytime outside of these hours are generally OK for driving except for popular sports events like a Bulls or Bears game, a concert, or other city-hosted events like parades and large festivals.

Also, note that Chicago is a bustling city that does a lot of business, so you will have to contend with semi-trucks, delivery vans, and heavy-duty trucks.


There is a saying in Chicago that “There are two seasons of the year, winter and construction.”

Plan your driving around the peak traffic hours and look for alternate routes via GPS. Even if you have extra time, don’t take it for granted.

Delays during construction are inevitable (and frustrating when the traffic is reduced from 4 to 1 lane)! There may also be delays caused by unexpected accidents or slowdowns caused by emergency vehicles.


Parking is always a challenge in the city and it’s very expensive and fees for parking violations are hefty. The best way to locate a garage is via SpotHero.com. You can find discounted fees for early arrivals (before 7 AM) but the hours you are allowed to stay for the discounted price is usually limited.

If you are staying in the downtown area and have a parking spot, I suggest you leave the car and use public transportation during your stay. Getting around Chicago is very easy, and you will save more money by avoiding the expense of additional parking.

If you do need to use a car, familiarize yourself with street parking regulations. There is rarely free street parking and just about every parking space downtown is metered. Look for the meter posts near the end of each block to pay for parking. The machines accept cash and credit cards.

When parking in neighborhoods, you will find that some require a permit or vehicle sticker. In winter, the lack of snow removal makes it difficult to find parking so residents will “reserve” spots with chairs, cones, or anything they can find. My advice is to avoid using these spots or you may risk retaliation.

Lastly, if driving in Chicago intimidates you, stay in the right-most lane or use the side streets. Avoid the road rage caused by speeding drivers who don’t use good driving etiquette. Try not to block cars who are trying to cross the main road from alleys, parking lots, or turning lanes.

Keeping these lesser-known aspects in mind will help ensure a smoother and stress-free driving experience in the bustling streets of Chicago.

Road Trip Safety Tips

While embarking on a road trip to Chicago, it’s crucial to prioritize safety. Read further for some essential safety tips to ensure a smooth and secure road trip.

Check Your Vehicle Condition

Before hitting the road, inspect your vehicle’s tires, brakes, lights, and fluids. Ensure everything is in good working order and consider getting a professional mechanic to perform a thorough inspection.

Plan the Route

Plan your route in advance, considering traffic conditions and any road closures. Utilize GPS navigation or maps to avoid getting lost and save time.

Share Your Itinerary with Family and Friends

Inform a trusted friend or family member about your road trip itinerary. Provide them with details of your planned route, accommodation, and expected arrival times. This way, someone will be aware of your whereabouts. Looking for more to do? Review some recommendations in our ultimate guide to Chicago.

Take Regular Breaks

Long drives can be tiring, so take regular breaks to stretch your legs, have a snack, and rest. Fatigue can impair your driving abilities, so it’s essential to stay alert and well-rested.

Stay Alert and Avoid Distractions

Keep your focus on the road and avoid distractions such as texting, eating, or adjusting the radio while driving. Remember, safety should always be your top priority.

Follow Traffic Laws

Observe and follow all traffic laws and regulations, including speed limits, seatbelt usage, and traffic signals. Be mindful of other drivers and pedestrians to ensure everyone’s safety on the road. When in doubt, review the rules of the road for Illinois.

Itineraries by Car: Scenic Drives in Chicago

Once you’ve reached Chicago, there are several iconic attractions you shouldn’t miss. Here are some must-see places that will make your road trip unforgettable.

Lake Shore Drive

Take a leisurely drive along Lake Shore Drive, which stretches along the beautiful shoreline of Lake Michigan. Enjoy stunning views of the lake, the city skyline, and iconic landmarks like Navy Pier and Grant Park.

Lake Shore Drive is about 16 miles long. You can start at 67th Street in the South Shore neighborhood and goes north to Hollywood Avenue.

The Magnificent Mile

Cruise along North Michigan Avenue, known as the Magnificent Mile. Marvel at the impressive architecture, luxury boutiques, and iconic landmarks as you drive through this bustling shopping district.

The Magnificent Mile is one mile long and starts at the Chicago River and extends north to Oak Street Beach.

The Outer Drive

The Outer Drive is also known as South Lake Shore Drive. This scenic route takes you through the southern part of the city, offering picturesque views of the lake, harbors, and the Museum Campus which consists of The Field Museum, the John G. Shedd Aquarium, and the Adler Planetarium.

The Outer Drive starts at East Jackson Drive and extends south to East 67th Street. It is in the southern part of Lake Shore Drive.

Green Bay Road

Head north of the city and take a drive on Green Bay Road. This road offers a scenic journey through the charming suburbs, lined with beautiful homes, parks, and quaint downtown areas.

Green Bay Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Skokie, Wilmette, Winnetka, Glencoe, Highland Park, Lake Forest, Waukegan, and Zion. These are great towns to explore outside of Chicago during your road trip.

Sheridan Road

Embark on a drive along Sheridan Road, which runs parallel to Lake Michigan. This picturesque route takes you through charming neighborhoods, historic mansions, and scenic lakefront parks.

Sheridan Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Bluff, Lake Forest, North Chicago, and Waukegan. You make want to include a visit to some of these towns during your Chicago road trip.

Chicago Skyway

Experience a unique perspective of the city by driving on the Chicago Skyway. This elevated toll road offers fantastic views of the downtown area and provides a smooth route to the neighboring state of Indiana for a day drive.

FAQs for a Chicago Road Trip

What is the driving distance to Chicago?

The driving distance to Chicago varies depending on your starting point. Use a reliable navigation tool or map application to get the most accurate distance information.

Are there any tolls on the way to Chicago?

Yes, there are tolls on some highways leading to Chicago. Make sure to carry cash or have an electronic tolling device like an I-PASS or E-ZPass for seamless travel.

How many days should I plan for a Chicago road trip?

The ideal duration for a Chicago road trip depends on your interests and the attractions you want to explore. A minimum of 3-4 days is recommended to cover the major highlights, but extending your stay allows for a more immersive experience.

Can I find parking easily in downtown Chicago?

Parking in downtown Chicago can be challenging, especially during peak hours. It’s advisable to research parking options in advance of your road trip and consider using public transportation or ride-sharing services to navigate the city.

What are some offbeat attractions in Chicago?

Apart from the popular landmarks, you can explore offbeat attractions like the Garfield Park Conservatory, and 360 Chicago Observation Deck, or take a street art tour in neighborhoods like Pilsen and Wicker Park.

Final Thoughts on a Chicago Road Trip

A road trip offers an incredible adventure filled with iconic Chicago attractions, delicious food, vibrant culture, and memorable experiences.

By packing essential items, following safety tips, and planning your itinerary, you can make the most of your journey.

Don’t forget to create your Chicago road-trip itinerary or read some of our recommendations for a perfect blend of vacation activities, iconic sights, cozy accommodations, and unique experiences.

Explore Millennium Park and Navy Pier, dive into the city’s vibrant culture, and immerse yourself in art at the Art Institute of Chicago.

When it comes to accommodations, choose from downtown hotels for convenience or boutique options for a personalized touch. Experiencing one of the best neighborhoods in Chicago will also create a memorable stay.

Indulge in deep-dish pizza (don’t forget to invite me), take an architecture boat tour, and catch a thrilling sports event. Chicago offers a road trip experience like no other, where every moment can be filled with excitement and discovery.

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