Chicago Travel: 100 Questions Answered based on NeemTime research
Getting There & Around
Q: What’s the best airport to fly into for Chicago?
A: O’Hare (ORD) is the larger international airport with more options, but Midway (MDW) is closer to downtown and often easier to navigate for domestic flights.
Q: How do I get from O’Hare to downtown?
A: The CTA Blue Line train is the most cost-effective and efficient way. Taxis/rideshares are also available but more expensive.
Q: How do I get from Midway to downtown?
A: The CTA Orange Line train is direct and easy. Taxis/rideshares are also an option.
Q: Is public transportation good in Chicago?
A: Yes, the CTA (Chicago Transit Authority) train (L) and bus system is excellent and covers most major areas.
Q: Should I buy a Ventra card for public transport?
A: Yes, it’s convenient. You can load it with daily or multi-day passes, or just pay per ride. You can also use contactless credit/debit cards directly at the turnstiles.
Q: Is it safe to walk around downtown at night?
A: Generally yes, especially in well-trafficked areas like River North, the Loop, and Michigan Avenue. Be aware of your surroundings, like in any major city.
Q: Do I need a car in Chicago?
A: No, in fact, it’s often more of a hassle due to traffic and expensive parking. Public transport, walking, and rideshares are sufficient.
Q: What’s the best way to get from one neighborhood to another if not by train?
A: Buses are great for cross-town travel or routes not directly on an ‘L’ line. Rideshares (Uber/Lyft) are also readily available.
Q: How accessible is Chicago for someone with mobility issues?
A: Many CTA stations have elevators, and buses are accessible. Newer attractions and buildings are generally ADA compliant, but some older establishments might be challenging.
Q: Are bike shares (Divvy) a good option for tourists?
A: Yes, for exploring specific areas like the lakefront trail or certain neighborhoods, but be mindful of traffic.
Accommodation
Q: What’s the best neighborhood to stay in for a first-time visitor?
A: The Loop, River North, and Magnificent Mile are central, close to attractions, and offer many hotel options.
Q: Are there budget-friendly hotel options in Chicago?
A: While central hotels can be pricey, look for options in areas like Streeterville, Printer’s Row, or consider hostels for even cheaper stays.
Q: Is it safe to stay in an Airbnb in Chicago?
A: Generally yes, but check reviews carefully. Some neighborhoods might have restrictions or be less convenient for tourists.
Q: What’s the deal with hotel taxes in Chicago?
A: Be aware that hotel taxes can add a significant amount to your bill, often around 17.4%.
Q: Any recommendations for hotels with great views?
A: The Langham, Trump International Hotel & Tower, LondonHouse, and many hotels along Michigan Avenue offer excellent river or lake views.
When to Visit
Q: When is the best time to visit Chicago?
A: Late spring (May-early June) and early fall (September-October) offer pleasant weather, fewer crowds than summer, and various festivals.
Q: Is Chicago very cold in winter?
A: Yes, winters are notoriously cold with snow and wind. Be prepared with warm layers if visiting between November and March.
Q: What’s Chicago like in summer?
A: Hot and humid, but vibrant with street festivals, outdoor concerts, and lake activities. It’s peak tourist season.
Q: What’s the deal with the “windy city” nickname?
A: It primarily refers to its historical political rhetoric, but the city can indeed be quite windy, especially along the lakefront.
Q: Are there any specific events or festivals I should plan my trip around?
A: Lollapalooza, Taste of Chicago, Pitchfork Music Festival, Pride Parade, and various neighborhood street festivals (e.g., Taste of Lincoln Avenue).
Must-See Attractions & Activities
Q: What are the absolute must-do attractions for a first-timer?
A: Art Institute of Chicago, Architectural Boat Tour, Millennium Park (The Bean), Skydeck Willis Tower, and a deep-dish pizza experience.
Q: Is the Skydeck (Willis Tower) worth it, or is 360 Chicago (Hancock) better?
A: Both offer great views. Skydeck has the Ledge (glass boxes). 360 Chicago (John Hancock Center) has Tilt! and often shorter lines, plus a bar with views. Many prefer 360 for the overall experience.
Q: Which architectural boat tour company is best?
A: Chicago Architecture Center River Cruise (formerly Chicago Architecture Foundation) is consistently recommended for its knowledgeable guides and in-depth information. Shoreline and Wendella are also popular.
Q: What’s there to do in Millennium Park besides The Bean?
A: Crown Fountain, Jay Pritzker Pavilion (free concerts in summer), Lurie Garden, and easy access to Maggie Daley Park.
Q: Is Navy Pier worth visiting?
A: It’s very touristy. Good for families with kids (Centennial Wheel, Chicago Children’s Museum) but can be crowded and a bit kitschy. Some find it skippable.
Q: What museums should I visit if I only have time for one or two?
A: Art Institute of Chicago is world-class. Field Museum (natural history) and Museum of Science and Industry are also excellent choices, depending on your interests.
Q: Is the Shedd Aquarium worth the price?
A: For marine life enthusiasts, yes. It’s a large, impressive aquarium. Buy tickets in advance to save time.
Q: What’s the best way to experience Lake Michigan?
A: Walk or bike the Lakefront Trail, visit a beach (North Avenue, Ohio Street), or take a boat tour.
Q: Any recommendations for free things to do?
A: Millennium Park, Lincoln Park Zoo (free!), walking the Lakefront Trail, Browse the Chicago Cultural Center, various free events in summer parks.
Q: Is the Lincoln Park Zoo worth visiting?
A: Absolutely! It’s one of the few remaining free zoos in the country and beautifully maintained.
Q: What’s there to do along the Magnificent Mile?
A: High-end shopping, dining, historic architecture, and access to other attractions.
Q: How much time should I dedicate to the Art Institute of Chicago?
A: At least 3-4 hours, but you could easily spend a full day if you want to see everything.
Q: Are there any good hidden gems or lesser-known attractions?
A: Frank Lloyd Wright Home and Studio (Oak Park), Garfield Park Conservatory, National Museum of Mexican Art (free), Glessner House Museum.
Q: What’s the best way to see the city lights at night?
A: Go up 360 Chicago or Skydeck, take a night architectural boat tour, or walk along the Chicago Riverwalk.
Q: Are there any good day trips from Chicago?
A: Milwaukee (by train), Indiana Dunes National Park, Starved Rock State Park, or Oak Park (Frank Lloyd Wright).
Food & Drink
Q: Where should I get deep-dish pizza? Giordano’s, Lou Malnati’s, or Pequod’s?
A: This is the eternal debate! Lou Malnati’s for butter crust, Giordano’s for classic thick cheese, Pequod’s for caramelized crust. Try them all if you can!
Q: What about Chicago-style hot dogs? Where’s the best place?
A: Portillo’s is a classic chain, but also check out smaller, local spots like Gene & Jude’s (no ketchup!) or Superdawg.
Q: What are other essential Chicago foods besides pizza and hot dogs?
A: Italian beef sandwich (Al’s Beef, Portillo’s), Garrett Popcorn Mix (cheese and caramel), Jibarito sandwich.
Q: Any recommendations for fine dining?
A: Alinea (molecular gastronomy), Smyth, Ever, Oriole, Girl & The Goat, Boka. Chicago has many Michelin-starred restaurants.
Q: Where can I find good, affordable food?
A: Food trucks, ethnic restaurants in neighborhoods like Pilsen (Mexican) or Argyle Street (Vietnamese), and casual eateries.
Q: What are some good places for brunch?
A: The Allis, Beatrix, Wildberry Pancakes and Cafe, Cindy’s Rooftop (for views).
Q: Best breweries or craft beer spots?
A: Revolution Brewing, Half Acre Beer Company, Goose Island (original Clybourn location), and numerous smaller taprooms in Logan Square or Avondale.
Q: Any good rooftop bars with views?
A: Cindy’s Rooftop (Chicago Athletic Association Hotel), LondonHouse Rooftop, LH Rooftop (LondonHouse), The J. Parker (Hotel Lincoln).
Q: What’s a good place for a classic Chicago steakhouse experience?
A: Gibsons Bar & Steakhouse, RPM Steak, Chicago Cut Steakhouse.
Q: Where can I get good breakfast near downtown?
A: Wildberry Pancakes and Cafe, Beatrix, Ann Sather (for cinnamon rolls).
Neighborhoods to Explore
Q: What’s worth seeing in Lincoln Park?
A: Lincoln Park Zoo (free!), Lincoln Park Conservatory, Peggy Notebaert Nature Museum, North Avenue Beach, charming brownstones.
Q: Is Pilsen worth visiting for tourists?
A: Yes, for its vibrant Mexican culture, incredible murals, National Museum of Mexican Art, and great food.
Q: What’s the vibe in Logan Square?
A: Hipster, trendy, with lots of great restaurants, bars, breweries, and a beautiful boulevard.
Q: Should I venture out to Hyde Park? What’s there?
A: Home to the University of Chicago, Museum of Science and Industry, Frank Lloyd Wright’s Robie House, and President Obama’s former home. Worth it if you have specific interests there.
Q: What’s there to do in Wicker Park/Bucktown?
A: Indie boutiques, vintage shops, lively bars, and excellent restaurants. Great for people-watching.
Practical Advice & Safety
Q: How much should I budget for a trip to Chicago?
A: Highly variable, but generally $150-$300+ per person per day, depending on accommodation, dining, and activities.
Q: Is Chicago safe for solo female travelers?
A: Generally yes, especially in tourist areas. Exercise common sense, be aware of your surroundings, and use reputable transportation.
Q: What’s the tipping etiquette in Chicago?
A: Standard US tipping: 15-20% for waitstaff/bartenders, 15-20% for rideshares, $2-5 per bag for porters.
Q: How do I avoid tourist traps?
A: Do your research, read reviews, and ask locals. Be wary of places that feel overly generic or are solely focused on souvenirs.
Q: What’s the best way to buy tickets for attractions?
A: Buy online in advance, especially for popular attractions, to save time and sometimes money. Consider a CityPASS if you plan to visit multiple major attractions.
Q: Is the CityPASS worth it?
A: It can be if you plan to visit at least 3-4 of the included attractions (Shedd Aquarium, Skydeck, Field Museum, Art Institute, Museum of Science and Industry, 360 Chicago). Do the math for your specific itinerary.
Q: What should I pack for Chicago?
A: Layers are key, regardless of season. Comfortable walking shoes are a must. A good rain jacket/umbrella is always wise.
Q: Is it easy to find restrooms in downtown Chicago?
A: Hotels, department stores, and museums typically have public restrooms. Some coffee shops or fast-food places will too.
Q: Are there any good walking tours besides the architectural one?
A: Yes, various historical, food, or neighborhood-specific walking tours are available. Free Tours by Foot offers pay-what-you-wish options.
Q: What’s the best way to get around if I have limited mobility?
A: Taxis/rideshares are convenient. Many CTA buses and some ‘L’ stations are accessible. Plan routes using the CTA’s accessibility features.
Q: How can I save money on food?
A: Pack snacks, eat lunch at casual spots, take advantage of happy hour deals, and consider cooking if you have an Airbnb with a kitchen.
Q: What’s the deal with traffic in Chicago?
A: It can be notoriously bad, especially during rush hour. Avoid driving if possible, and factor in extra time for rideshares.
Q: Are there any good grocery stores downtown?
A: Whole Foods, Jewel-Osco, and Target have locations downtown or easily accessible.
Q: What kind of power outlets do they use in Chicago/US?
A: Type A and B, 120V.
Q: How much cash do I need?
A: Most places accept credit cards. Keep a small amount of cash for tips or small purchases, but it’s not essential.
Q: Is it safe to carry a backpack on the ‘L’ train?
A: Yes, but keep it in front of you in crowded situations to deter pickpockets.
Q: What if I have an emergency? (medical, police)
A: Dial 911 for emergencies. Major hospitals are easily accessible downtown.
Q: Are there any specific scams tourists should be aware of?
A: Be wary of people asking for money aggressively, especially near popular attractions. Use official taxi stands or rideshare apps.
Q: What’s the general vibe of Chicagoans towards tourists?
A: Generally friendly and welcoming! They’re proud of their city.
Q: Is it easy to navigate Chicago using a smartphone?
A: Absolutely. Google Maps, Citymapper, and the CTA app are invaluable for public transit.
Shopping & Souvenirs
Q: Where should I go for shopping besides the Magnificent Mile?
A: State Street (Macy’s flagship), Armitage/Halsted in Lincoln Park (boutiques), Bucktown/Wicker Park (indie shops).
Q: What are some unique Chicago souvenirs?
A: Garrett Popcorn, local craft beer, Cubs/Sox merchandise, items from the Art Institute gift shop, or something related to architecture.
Q: Are there any good farmers markets?
A: Green City Market (Lincoln Park, summer) is popular. Various neighborhood markets operate during warmer months.
Q: Where can I buy Chicago sports team merchandise?
A: Team stores near the stadiums (Wrigleyville for Cubs, Guaranteed Rate Field for White Sox), or many sports apparel stores on Michigan Avenue.
Q: Any good bookstores to visit?
A: Powell’s Books, Myopic Books, The Book Cellar.
Culture & Entertainment
Q: What’s the theater scene like in Chicago?
A: Excellent! Home to numerous award-winning theaters, including Steppenwolf, Goodman Theatre, and Broadway in Chicago productions.
Q: Where can I see live music?
A: Buddy Guy’s Legends (blues), Kingston Mines (blues), Green Mill Cocktail Lounge (jazz), Thalia Hall, Empty Bottle, Schubas Tavern.
Q: Is there good comedy in Chicago?
A: Yes, Chicago is a comedy hub! The Second City and iO Theater (improv), Zanies, and The Laugh Factory for stand-up.
Q: Any recommendations for art galleries?
A: Besides the Art Institute, check out galleries in River North, West Loop, or Pilsen.
Q: What’s the best way to experience Chicago’s jazz/blues history?
A: Visit Buddy Guy’s Legends, Kingston Mines, Green Mill, or look for specific tours or historical markers.
Q: Are there any historical sites or landmarks beyond the main attractions?
A: Chicago Cultural Center, Pullman National Monument, Clarke House Museum, Old St. Patrick’s Church.
Q: What’s the best way to catch a Cubs game?
A: Buy tickets in advance, especially for popular games. Experience Wrigleyville before/after the game.
Q: How about a White Sox game?
A: Guaranteed Rate Field is on the South Side, easily accessible by Red Line. Often easier to get tickets than Cubs games.
Q: Are there any public art installations worth seeking out?
A: The Bean (Cloud Gate), Crown Fountain, Picasso sculpture (Daley Plaza), Flamingo (Calder sculpture), Agora (Grant Park).
Q: What’s the best place for people-watching?
A: Millennium Park, Michigan Avenue, Riverwalk, or any outdoor café.
Miscellaneous
Q: What’s the “L” train system like? Is it confusing?
A: It’s relatively easy to navigate once you understand the colored lines and directions (North/South/Loop).
Q: How early should I arrive at O’Hare for a domestic flight?
A: Typically 2 hours, 3 if checking bags or during peak travel times.
Q: What’s the typical weather forecast for [month]?
A: Consult a reliable weather app closer to your travel date, but generally:
Spring: Mild, variable, can be rainy.
Summer: Hot, humid, thunderstorms possible.
Fall: Crisp, pleasant, colorful.
Winter: Cold, snowy, windy.
Q: Are there public Wi-Fi hotspots available?
A: Many coffee shops, restaurants, and some public spaces offer free Wi-Fi.
Q: What’s the best way to get a local perspective on things to do?
A: Engage with locals at bars/restaurants, or strike up conversations.
Q: Is there anything unique about Chicago etiquette?
A: Stand on the right, walk on the left on escalators. Don’t put ketchup on a hot dog (seriously, don’t). Be patient on public transport.
Q: What are some good places for photos?
A: Millennium Park, Chicago Riverwalk, Navy Pier (at sunset), Museum Campus, Lincoln Park, architectural boat tour.
Q: Can I drink alcohol in public parks?
A: No, it is generally illegal to consume alcohol in public parks in Chicago.
Q: What’s the best way to beat the heat in summer?
A: Visit air-conditioned museums, take a boat tour on the lake, relax on a beach, or find a rooftop pool.
Q: How to stay warm in winter?
A: Layers, warm coat, hat, gloves, scarf. Duck into museums, shops, and warm restaurants.
Q: What’s the best way to enjoy the Chicago Riverwalk?
A: Walk along it, rent a kayak, grab a drink at one of the bars, or just sit and people-watch.
Q: Are there any good spots for kids besides Navy Pier?
A: Chicago Children’s Museum, Museum of Science and Industry, Field Museum (dinosaurs!), Lincoln Park Zoo, Maggie Daley Park (playgrounds).
Q: What’s the best time of day to visit The Bean (Cloud Gate) to avoid crowds?
A: Early morning right after sunrise, or late evening.
Q: Is it possible to see a show/concert spontaneously?
A: Yes, for some smaller venues or last-minute theater tickets, but for major acts or popular shows, it’s best to book in advance.
Q: What’s one piece of advice you’d give to someone visiting Chicago for the first time? * A: Wear comfortable shoes and be prepared to walk a lot! Embrace the public transport and enjoy the diverse neighborhoods.