Thinking about planning a trip to Chicago? Whether it’s your first time or a return visit, the Windy City can feel overwhelming with so much to see and do. As someone who once explored Chicago as a visitor and now navigates it like a local, I’ve learned the best ways to get here, get around, and find the perfect place to stay.
This guide covers transportation options, how to get from the airports and train station to downtown, an overview of Chicago’s best neighborhoods, and hotel recommendations for every budget—plus insider tips to help you make the most of your trip!
🛤️ How to Get to Chicago
Chicago is one of the most accessible cities in the U.S., with major highways, Amtrak train routes, intercity bus services, and two international airports. Here’s how to arrive stress-free. We’ve also prepared a handy guide to the Chicago CTA to help you navigate your way around the city using public transportaion.
🚆 Arriving by Amtrak: What to Know About Union Station
If you’re coming by train, Chicago’s Union Station is the main Amtrak hub, serving cities across the U.S., including New York, Washington, D.C., St. Louis, and Milwaukee.
📍 Address: 225 S Canal St, Chicago, IL 60606
CTA Train Access: The closest “L” train stations are Clinton (Blue Line) and Quincy (Brown, Orange, and Pink Lines)—just a short walk away.
Navigating Union Station: The station is large but well-marked. After disembarking, follow signs toward the Great Hall or street exits.
Getting to Your Hotel: Taxis line up outside the main entrance, and Uber/Lyft pickups are available nearby (check the app for exact zones).
🚌 Traveling to Chicago by Bus
Taking a Greyhound, Megabus, or FlixBus is one of the most affordable ways to get to Chicago. Buses connect from cities across the Midwest and beyond, dropping passengers near downtown.
- Greyhound Station – 📍630 W Harrison St, Chicago, IL 60607 (near Union Station, with easy CTA access).
- Megabus & FlixBus Stops – Pickup/drop-off locations vary, but many arrive near Chicago’s Loop or West Loop (check your ticket for exact locations).
💡 Tip: Many bus riders prefer Megabus or FlixBus for their cheaper fares and more comfortable seating than Greyhound. Book in advance for the best prices!
✈️ Flying Into Chicago: O’Hare vs. Midway Airports
Chicago is served by two major airports:
- O’Hare International Airport (ORD) – 📍10000 W O’Hare Ave, Chicago, IL 60666
- One of the busiest airports in the world, with CTA Blue Line service that takes about 45 minutes to downtown ($5 fare).
- Midway International Airport (MDW) – 📍5700 S Cicero Ave, Chicago, IL 60638
- A smaller airport that’s often easier to navigate, with CTA Orange Line service taking 30 minutes to downtown ($2.50 fare).
💡 Tip: If you’re taking a rideshare from O’Hare or Midway, follow signs for the designated pickup areas—these are separate from taxi stands.
🚗 Driving to Chicago: What to Know
If you’re planning to drive to Chicago, be prepared for tolls, traffic, and parking costs. Major highways leading into the city include I-90/I-94 (Dan Ryan/Kennedy Expressways), I-290 (Eisenhower Expressway), and I-55 (Stevenson Expressway).
To bypass downtown congestion, consider using the Illinois Tollway (I-294 Tri-State Tollway), which loops around the city and helps avoid rush-hour traffic. Expect to pay $5-$10 in tolls depending on your route. You can pay at each toll booth or consider purchasing an I-PASS or E-ZPass in advance to skip the lines or the toll booth. No cash? You can pay online within 14 days.
🚗 Parking Costs: Chicago hotels almost always charge for parking, with valet rates ranging from $50-$80 per night. If you’re looking for a more budget-friendly option, parking garages downtown typically cost $30-$50 per day. Apps like SpotHero let you book a space in advance, often at a discount—but keep in mind, this isn’t in-and-out parking, so you’ll need to commit to one spot.
💡 Tip: If you don’t need your car for sightseeing, park outside the city and take the CTA train in—it’s often cheaper and much less stressful! 🚆
🏙️ Chicago’s Best Neighborhoods to Explore
One of the things that really cemented my love for the city of Chicago is its neighborhoods. This is a city built for people, and Chicago’s diverse neighborhoods each have its own character. While downtown is a great starting point, venture beyond the Loop to get a real feel for the city.
The Loop & Downtown
- The heart of the city, home to Millennium Park, The Art Institute, and historic skyscrapers. Don’t miss the shops on State Street, including the iconic Marshall Field’s building – now a Macy’s. Block 73 also has shops like Zara and Anthropologie as well as a Molly’s Cupcakes.
- Ideal for first-time visitors who want to be within walking distance of major attractions.
River North
- Known for trendy restaurants, nightlife, and upscale shopping. This is my first pick for first-time visitors, because you are centrally located to so many great shops and resturants, as well as easy public transporation to other parts of the city. It’s also withing walking distance to the stunning Lake Michigan shoreline as well as the world-famous Chicago Riverwalk.
- Home to Chicago’s famous deep-dish pizza spots like Lou Malnati’s and Gino’s East.
Streeterville
- A waterfront neighborhood near Navy Pier and the Magnificent Mile. One of the highlights of Streeterville is the Museum of Contemporary Art, which boasts an amazing collection as well a hosting event and exhibitions.
- Great for families and visitors who want lakefront views. Like River North, Streeterville is also a very conventient spot for dining, shopping and accessing public transportation. You’ll also have a wide variety of Streeterville restaurants within steps.
Wicker Park & Logan Square
- Hipster and artsy areas full of independent boutiques, live music venues, and craft cocktail bars. Milwaukee Avenue is the main thoroughfare in Wicker Park, and you can easily spend a day wandering the boutiques and restaurants. My personal favorite spot in Wicker Park is Myopic Books, one of the best bookstores in Chicago, and the John Fluevog Shoes outpost here is a don’t-miss.
- A great spot for foodies and coffee lovers!
Pilsen & Little Village
- Rich in Mexican culture, street art, and authentic taquerias, Pilsen is a tight-knit community proud of its rich culture and it shows.
- Home to the National Museum of Mexican Art, and one of the most underrated sandwich and coffee shops in Chicago, the Mandala Cafe (1641 W 18th St, Chicago, IL 60608).
Chinatown
Just a quick Red Line ride from downtown, offering delicious dim sum, bubble tea, and traditional Chinese markets. Try MingHin Cuisine or Qing Xiang Yuan Dumplings, or my personal favorite, Joy Yee Kitchen.
🌳 Lincoln Park
A lively, green oasis just north of downtown, Lincoln Park blends city charm with nature. Stroll through Lincoln Park Zoo (free!), the stunning conservatory, and the lakefront trails. Perfect for brunch lovers and boutique shoppers! Don’t miss popular North Avenue beach, one of the most popular Chicago beaches in the summer; or The Chicago History musuem on North Ave, where you can learn more about the fascinating history of Chicago. Try Cafe Ba-Ba-Reeba! for tapas or Homeslice for craft pizza and cocktails.
PRO TIP: If you’re exploring the Lincoln Park neighborhood with your children, be sure to check out our guide to the Best Things to Do in Lincoln Park with Kids.
Where to Stay in Chicago
Finding the right place to stay in Chicago depends on your budget and preferred location. Here are some of my favorite hotels in the city in different price ranges.
✨ Luxury Hotels ($300+)
- The Langham Chicago – 📍330 N Wabash Ave, Chicago, IL 60611
- A five-star riverfront hotel with stunning skyline views and an award-winning spa.
- Pendry Chicago – 📍230 N Michigan Ave, Chicago, IL 60601
- A stylish boutique hotel in a historic Art Deco building, just steps from Millennium Park.
🏨Boutique Hotels ($200-$300)
- The Talbott – 📍20 E Delaware Pl, Chicago, IL 60611
- A sophisticated Gold Coast gem with elegant rooms and a cozy, European-inspired vibe.
- Claridge House – 📍1244 N Dearborn Pkwy, Chicago, IL 60610
- A chic retreat in Lincoln Park, perfect for exploring nearby shops, cafés, and the lakefront.
Mid-Range Hotels ($150-$300)
- Hotel EMC2 – 📍228 E Ontario St, Chicago, IL 60611
- A trendy hotel in Streeterville with high-tech amenities and a unique science-meets-art theme.
- Chicago Athletic Association – 📍12 S Michigan Ave, Chicago, IL 60603
- A historic hotel with a speakeasy bar and rooftop views of Millennium Park.
Budget Hotels ($100-$150)
- Hampton Inn Chicago Downtown West Loop – 📍116 N Jefferson St, Chicago, IL 60661
- A modern, budget-friendly hotel with free breakfast and a rooftop patio.
- Club Quarters Hotel Wacker at Michigan – 📍75 E Wacker Dr, Chicago, IL 60601
- A no-frills, affordable stay right on the river.
Final Thoughts
Planning a trip to Chicago doesn’t have to be overwhelming, and I think with this important information you’ll be just fine. With multiple transportation options, diverse neighborhoods, and accommodations for every budget, you’ll find a way to make your visit smooth and stress-free. Questions? Please use the comment section below to reach out.