Chicago Travel Tips: Insider Advice for First-Time Visitors
Heading to Chicago? From Unpredictable Weather to the Best Neighborhoods, Here’s Drives & Detours’ Guide to Exploring the Windy City Like a Local
Chicago’s soaring skyline, rich history, and vibrant neighborhoods make it a must-visit city — Christopher Alvarenga / Unsplash
Chicago, known as the Windy City, is one of America’s most dynamic urban destinations. Its soaring skyline, rich history, and vibrant neighborhoods make it a must-visit city.
Navigating Chicago can be a little overwhelming for first-time travelers. Between sudden weather changes, sprawling neighborhoods, and dozens of iconic attractions, it helps to have some insider tips.
Drives & Detours' practical insights will help you get the most out of your trip, whether you’re here for a weekend or a longer stay.
Chicago Weather: Always Be Prepared
Bring a lightweight, waterproof jacket, a scarf, and comfortable shoes when you visit, just in case — Fineas Anton / Unsplash
Chicago’s weather is famously unpredictable. You could start your day in sunshine, only to find yourself caught in a sudden rain shower or chilly gust of wind along Lake Michigan.
This is especially true in spring and fall, when temperatures can fluctuate wildly within a single day. Even in summer, evenings can be surprisingly cool near the lakefront.
The local advice? Layer up. Bring a lightweight, waterproof jacket, a scarf, and comfortable shoes that can handle wet sidewalks.
Many people recommend keeping a small umbrella in your bag and always checking the forecast before heading out.
Choosing Where to Stay in Chicago
The Loop is close to the major attractions and always a good place to stay — Aveedibya Dey / Unsplash
Your choice of neighborhood can make or break your Chicago experience.
First-time visitors often stick to downtown areas, such as the Loop, River North, and Gold Coast.
These neighborhoods place you close to major attractions such as Millennium Park, the Art Institute, and the Chicago Riverwalk.
Hotels here vary between luxury high-rises and boutique stays, giving you plenty of options depending on your budget.
Neighborhoods like Logan Square, Wicker Park, and Lincoln Park offer a blend of residential charm, trendy cafes, and independent boutiques if you’re seeking a more local vibe.
These areas are ideal for travelers who want to explore Chicago beyond the typical tourist path.
On the flip side, some neighborhoods on the South and West Sides can feel less welcoming to visitors, especially at night, so it’s wise to research and stick to well-traveled areas.
Getting Around Chicago
The L train makes Chicago easy to navigate without a car — Sawyer Bengtson / Unsplash
Chicago has a robust public transit system, which can save you both time and money.
The CTA L trains run frequently and cover most of the city’s key neighborhoods. A Ventra card makes hopping on buses and trains easy, and it’s much simpler than dealing with single-ride tickets.
Walking is also a great way to explore, especially in areas such as River North, the Loop, and along the Riverwalk.
Just keep in mind that Chicago streets are laid out on a grid, but the river and freeway overpasses can be confusing at first.
Locals often warn tourists to avoid Lower Wacker Drive, an underground street along the river that’s easy to get lost on and less safe at night.
Rideshares and taxis are plentiful but can be more expensive during rush hour. For those driving, be prepared for limited street parking downtown—garages are plentiful but pricey.
Family-Friendly Fun
Chicago is full of musuems, parks and activities to keep the kids entertained — Dulcey Lima / Unsplash
Chicago is very family-friendly. Lincoln Park Zoo is free, open year-round, and offers a fun, educational outing that kids love.
The Museum of Science and Industry is another must-visit. Its hands-on exhibits range from a real U-505 submarine to interactive science experiments that entertain all ages.
For outdoor fun, Millennium Park and the Chicago Riverwalk provide plenty of space to run, explore, and take in public art.
The city also hosts seasonal events like ice skating in winter and free summer concerts at Grant Park, making it a great destination for families.
Chicago’s Neighborhoods and Hidden Gems
The Riverwalk is filled with cafes, public art, and small docks — John Benitez / Unsplash
While attractions like Navy Pier and the Magnificent Mile are popular, Chicago is full of lesser-known spots worth exploring.
The Chicago Riverwalk is a perfect example. This scenic pedestrian path along the river is filled with cafes, public art, and small docks where you can watch boats glide by. It’s a peaceful way to experience the city without the crowds of tourist hubs.
Foodies shouldn’t miss neighborhoods like Logan Square or Pilsen. Lula Café in Logan Square serves inventive farm-to-table cuisine, while Pilsen offers a vibrant Mexican-American culinary scene and colorful street murals.
These areas give visitors a taste of Chicago’s authentic local culture.
Food & Drink Tips
Chicago may be famous for its pizza, but the city has much more to offer foodies — Matt Antonioli / Unsplash
Chicago is famous for deep-dish pizza, hot dogs, and Italian beef sandwiches, but don’t stop there.
Venture into smaller, locally-owned restaurants to discover hidden culinary gems. Places like Mirra, a South Asian-Mexican fusion spot in Logan Square, or Hooligan, a seafood and wine bar at Time Out Market, have become must-try stops for locals and visitors alike.
When dining out, remember that tipping is expected—typically 15-20% of the bill. Also, many restaurants in Chicago are cashless, so carry a credit card or a mobile payment option.
Chicago’s Events, Festivals, and Seasonal Advice
Chicago’s calendar is packed with events year-round, offering something for every type of traveler.
Summer— Food Festivals, Jazz, and Fireworks
Chicago is at its most alive during summer, but you’ll always find a spot to relax in — Miguel Angel Sanz / Unsplash
Summer is the city’s most vibrant season, with longer daylight hours and warm temperatures perfect for outdoor adventures.
Iconic events such as Taste of Chicago, the world’s largest food festival, give visitors the chance to sample local favorites, from deep-dish pizza to gourmet street food.
Music lovers can enjoy free concerts in Grant Park or catch jazz and blues performances across the city’s many live venues.
Summer also brings spectacular fireworks displays over Lake Michigan, particularly on the Fourth of July and during special weekend events at Navy Pier.
Fall Foliage, Oktoberfest, and Architecture
Food and cultural festivals fill the city’s streets during fall — Mary West / Unsplash
Fall is one of the most picturesque times to visit Chicago. The leaves along the lakefront, in Lincoln Park, and in the city’s many neighborhoods turn brilliant shades of orange, red, and gold.
Seasonal events abound, from Oktoberfest celebrations to cultural street festivals that showcase local art, food, and music.
Fall is also ideal for architecture and walking tours, as the cooler weather makes exploring the city on foot much more comfortable.
Winter—Christkindlmarket, Ice Skating, and Cozy Retreats
Chicago’s winters are cold, but very charming — Alex Azabache / Unsplash
Winter in Chicago can be cold and windy, especially along the lakeshore, but it’s also a season of charm.
Downtown transforms with holiday lights, festive markets, and ice-skating rinks, including the popular McCormick Tribune Ice Rink in Millennium Park.
Winter festivals such as the Christkindlmarket, a German-inspired Christmas market, bring a warm and festive atmosphere where visitors can shop for unique gifts, enjoy seasonal treats, and sip on hot drinks.
Indoor attractions like museums, theaters, and restaurants offer cozy retreats from the chill, making winter an unexpectedly enjoyable time to explore the city.
Spring—Flower Shows and Lakefront Walks
Spring is perfect for walks along the river and around the lakes — Benjamin R / Unsplash
Spring is a time of renewal in Chicago, as the city thaws and gardens bloom.
The Chicago Flower & Garden Show and various neighborhood spring festivals celebrate the season with vibrant displays and family-friendly activities.
Spring is also the perfect season for lakefront walks, bike rides along the Lakefront Trail, and early outdoor dining as patios reopen.
Rain can be frequent in March and April, so packing a light rain jacket and umbrella is highly recommended.
Chicago Has a Year-Round Calendar of Activities
Planning your visit to Chicago around the city’s festivals can transform your visit — Anton Melekh / Unsplash
No matter when you visit, Chicago’s seasonal events provide a wonderful lens into the city’s culture and community.
Planning your trip around festivals or seasonal highlights can transform a standard visit into a truly memorable experience.
For travelers looking for a mix of indoor and outdoor activities, Chicago’s year-round calendar ensures there’s always something happening—from gourmet food festivals and cultural parades to music, theater, and family-friendly attractions.
Shopping and Souvenirs
Whatever you are looking for, Chicago is full of incredible shopping — Pedro Lastra / Unsplash
Chicago is home to unique shopping districts.
The Magnificent Mile offers high-end shopping, while neighborhoods like Andersonville and Wicker Park feature indie boutiques and vintage finds.
Don’t miss local markets like Green City Market for artisanal goods, produce, and local crafts. These spots are perfect for picking up souvenirs or gifts that are truly Chicagoan.
Enjoy Chicago Like a Local
There is always something new to discover in Chicago — Patrick Robert Doyle / Unsplash
Chicago is a city that rewards curiosity. Whether you’re wandering the Riverwalk, exploring historic architecture, sampling the local cuisine, or simply people-watching in a lakeside park, there’s always something new to discover.
You’ll experience the Windy City in a way that feels both authentic and unforgettable by planning ahead, packing wisely, and venturing beyond the usual tourist routes.
Remember: layers, comfortable shoes, and an open mind are your best friends here. Chicago may surprise you with sudden weather, bustling neighborhoods, and hidden gems around every corner — and that’s exactly what makes it such a memorable city to visit.
With Drives & Detours tips in hand, you’re ready to enjoy Chicago like a local and make the most of every moment in this dynamic, ever-changing city.
Discover Chicago on Your Own Schedule With Drives & Detours
Drives & Detours’ self-guided tours are packed with insider insights and allow you to explore Chicago on your terms — Joss Broward / Unsplash
Experience the Windy City at your own pace with Drives & Detours’ self-guided tours. Designed for convenience and full offline access, these tours are packed with insider insights and allow you to explore the city on your terms.
Purchase your tour ahead of time or start it directly through the app whenever it fits your schedule. Each route guides you through Chicago’s must-see landmarks as well as lesser-known spots, giving you a full picture of the city’s rich history and vibrant culture.
With Drives & Detours, you’ll find the hidden gems, neighborhood favorites, and local experiences that make Chicago a city worth exploring again and again.
