Chicago Trip Planner
Why Visit Chicago: Top Reasons & Highlights
Chicago's vibrant art scene captivates travelers, with reviews often praising the Art Institute and Millennium Park. Visitors relish in the diverse food offerings, from deep-dish pizza to upscale dining. Lakefront activities and historic architecture are must-sees. Pilot simplifies planning with curated itineraries tailored to your tastes, ensuring an organized, authentic experience.
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What to do in Chicago
With so much to do and so much to see, use Pilot to make your plan to make the most of your trip.
Explore top things to do
- 🌇 Explore the views at Skydeck Chicago - 🎭 Catch a show in the vibrant theater district - 🖼️ Visit The Art Institute of Chicago - 🌳 Stroll through Millennium Park, home of "The Bean" - ⚾ Experience a Cubs game at Wrigley Field - 🚲 Cycle along the Lakefront Trail - 🍕 Try deep-dish pizza at Lou Malnati's Use Pilot to effortlessly plan your organized Chicago itinerary.
Find the perfect neighborhood to stay in
🌆 Explore The Loop for a bustling city vibe. Visitors highlight its convenient access to attractions and impressive architecture. 🍕 Head to Wicker Park for eclectic dining and vibrant nightlife. It's a hub for foodies and trendsetters. 🎨 Discover Pilsen for its colorful street art and authentic Mexican cuisine. Travelers enjoy the cultural immersion. 🎶 Visit Lincoln Park for its expansive green spaces and the free zoo. Families love its laid-back charm. 🏨 Use Pilot to find the perfect hotel and snag exclusive booking deals.
Discover the best food and drink
- 🍕 Chicago is famous for its deep-dish pizza. Giordano’s and Lou Malnati’s are must-visits for this cheesy, thick delight. - 🍔 The Italian beef sandwich is another specialty. Al’s Beef is a local favorite spot for this savory treat. - 🌭 Don’t miss the Chicago-style hot dog, topped with a “salad” of diverse tastes. Portillo’s serves a classic version. - 🍰 Finish with a slice of Eli's Cheesecake, a Chicago staple that satisfies sweet cravings. -🍽️ Pilot can help you organize these culinary experiences for a delicious visit to Chicago.
In popular culture
🍕 Chicago's crime series 'Chicago Fire,' 'Chicago P.D.,' and 'Chicago Med' captivate viewers with gripping stories. 🎥 'The Dark Knight' transformed Chicago into Gotham City, using locations like Navy Pier and Willis Tower. 🎶 Kanye West's 'Homecoming' celebrates Chicago’s vibe and culture. 🏙️ 'Ferris Bueller's Day Off' explores the city, showcasing landmarks like the Art Institute and Wrigley Field. 📺 'Shameless' captures the city’s character, set in Canaryville and the Back of the Yards. 📚 Studs Terkel and Nelson Algren wrote about the city's gritty realism. 🎬 'My Best Friend's Wedding' features iconic scenes shot at O’Hare International Airport.
Chicago at a glance
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What reviews say
- Great food scene with diverse options, especially deep-dish pizza and local favorites. - Visitors love the architecture, recommend architectural boat tours. - Friendly but fast-paced atmosphere; it's easy to get around. - Some warn about high prices and unpredictable weather. - Museums and parks are highly praised, especially The Art Institute. - Locals suggest exploring neighborhoods like Wicker Park for hidden gems. - Be mindful of safety, especially when exploring less touristy areas.
What reddit says
- Visitors praise Chicago's food scene. Try deep dish pizza and hot dogs for a local taste. - The architecture is stunning. Recommend the architecture river cruise for a unique view. - Museums like the Art Institute are must-visits. - Locals suggest exploring neighborhoods like Pilsen and Logan Square for vibrant culture. - Some travelers mention safety concerns. Stick to well-known, busy areas.
Travel tips and safety
- Chicago's public transportation is reliable. Invest in a Ventra card for easy travel. - Sales tax is about 10.25%—factor this into shopping budgets. - Lakefront Trail is perfect for biking and walking. - Totals with gratuity in restaurants can range from 15-20%. - Tipping cab drivers isn’t mandatory but 10-15% is courteous. It's generally safe but as with any big city, stay aware of your surroundings. Consult travel advisories for updated information as situations can change.
Getting around
- Use the "L" train: convenient, budget-friendly, kind of easy to navigate. - Fares: $2.50 per ride; unlimited ride passes available. - Rideshare/taxis: pricier, but great for late nights or outlying trips. - Walkable neighborhoods: River North, The Loop, Lincoln Park. - Divvy bike rentals: accessible, ideal for lakefront paths. Pilot can help you plan routes efficiently.
How much it costs to visit
Visiting Vancouver can fit a range of budgets. Here's a rough idea: Budget ($60-$100/day): - Hostel stay: $25-$40 - Meals from food trucks or casual spots: $10-$15 - Public transport pass: $10 - Free or low-cost activities: $5-$10 Mid-range ($150-$200/day): - 3-star hotel: $80-$120 - Dining at mid-range restaurants: $25-$40 - Public transport, occasional taxi: $15 - Activities like admission to attractions: $30 Luxury ($300+/day): - 5-star hotel: $200+ - Gourmet dining: $60+ - Transport via taxi or rental cars: $50 - Premium activities and entertainment: $100+ Prices vary at different times of year and during large events. Check Pilot to find current rates for hotels and activities.
What to do if you only have one day to visit
🍽️ Start your day with breakfast at Lou Mitchell's, a classic Chicago eatery known for its hearty meals. 🌳 Head to Millennium Park to see the iconic Cloud Gate (The Bean) and enjoy a walk around the park's gardens. 🎨 Spend an hour or two at the Art Institute of Chicago, home to a world-renowned art collection. 🌭 For lunch, grab a Chicago-style hot dog at Portillo's and savor this local favorite. 🏛️ Visit the Field Museum to explore its fascinating exhibits and see Sue, the famous T. rex. 🛍️ Stroll down the Magnificent Mile for some shopping and people-watching. 🚤 Take an architecture river cruise for unbeatable views and insights into the city's skyline. 🥂 Wind down with a drink at the Signature Lounge, located on the 96th floor of the John Hancock Center, offering stunning city views. Use Pilot to easily generate and map an itinerary like this for you for free in just a few clicks.
What to do if it rains
- ☔️ Check out the Art Institute of Chicago with its impressive art collection. It's perfect for exploring on a rainy day. - 🎭 Enjoy a show at Second City, the famous comedy club. Laughter will brighten any gloomy day. - 📚 Head to the Chicago Cultural Center for free exhibits and stunning architecture. - 🍲 Try a food tour at the indoor Chicago French Market for delicious local eats. - 🦈 Visit the Shedd Aquarium and discover incredible marine life. It's fascinating and fun indoors. - 🖥 Experience the Museum of Science and Industry with interactive exhibits and fun for all ages. - 🚂 Explore the free exhibits and play areas at Maggie Daley Park if you're dressed for the weather. - 🎶 Catch a jazz set at a cozy club like the Green Mill Lounge; a warm escape with rich history.
When to visit and how many days to spend
- Best to visit: Late May to June or September to October - Temp: 18-24°C (64-75°F) - Avoid: January to February - Temp: -3 to 2°C (26-36°F) - Climate: Humid continental - Biome: Temperate deciduous forest - Summer: Warm, humid - Winter: Cold, windy - Expect variation, pack layers - Enjoy food, architecture tours - Walk scenic Lakefront Trail - Embrace rainy days with museums
How to find events during your stay
- Check out Choose Chicago for events and festivals: choosechicago.com - Follow Chicago Reader for local happenings: chicagoreader.com - Monitor Block Club Chicago for neighborhood events: blockclubchicago.org - For live music and concerts, visit Do312: do312.com - Chicago Park District has seasonal events: chicagoparkdistrict.com - Follow @ChicagoUnderground for unique local events on Instagram - Listen to WBEZ Chicago for upcoming cultural activities: wbez.org
Before your trip, read the history
Chicago, nestled on the western shores of Lake Michigan, traces its origins to the early 1800s, when it was the site of the Potawatomi tribe. The area’s name was derived from "Checagou," a reference to the pungent wild leeks in the region. As a city, it was officially incorporated in 1837, quickly becoming a hub due to its strategic location by the Great Lakes and its booming trade via waterways and later railways. Visitors might appreciate that Chicago's progressive political leanings have shaped its social policies and culture for decades.From the Great Chicago Fire in 1871, which paved the way for the unique opportunity to rebuild with innovation, to the rise of notable figures like urban planner Daniel Burnham and architect Louis Sullivan, the city has always bounced back with resiliency. The legacy of political figures such as Mayor Richard J. Daley and President Barack Obama adds layers to its rich narrative. Exploring landmarks like the Willis Tower or Millennium Park, one connects to this city's profound history and contribution, both as a cultural titan and an economic powerhouse in the Midwest.
