Welcome to my hometown the Windy City! As a first-time visitor, you’re in for an exciting adventure in one of North America’s most dynamic cities. Chicago is a city that seamlessly blends historic charm with modern flair, offering something for everyone.
From the illustrious skyline graced by the Sears Tower (Willis Tower) to the picturesque shores of Lake Michigan, there’s no shortage of memorable experiences. Whether you’re wandering through Millennium Park, exploring the diverse neighborhoods, or indulging in the world-renowned culinary scene, Chicago promises an unforgettable journey.
As your travel-savvy big sister, I’m here to guide you through the best places to stay, ensuring your trip is as seamless and enjoyable as possible. So pack your bags, grab your travel buddy (furry friends included), and get ready to discover the heart of the Midwest.
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How To Get Around Chicago
It is costly to park anywhere in Chicago with 2.7 million people. The City is on a perfect grid system, making getting lost nearly impossible. If you get lost, you’re a ding dong.
After the Great Chicago Fire, it was reimagined as the pinnacle of modernity. Here’s a pro tip. Madison Street divides Chicago north and south, while State Street divides it east and west. The State and Madison intersection in downtown Chicago marks the starting point of Chicago’s grid system.
Chicago Transit Authority (CTA)
Chicago has the second-largest public transportation system in the country. The CTA operates Chicago’s eight “L” train lines and 129 bus routes. Locals will call it the “L” because most train tracks are elevated. Two lines in Chicago operate 24/7: the Blue Line, which connects Chicago O’Hare International Airport and downtown, and the Red Line, with service between the North and South Sides via downtown.
Pro tip: Use the reloadable Ventra Card or Unlimited Ride Pass for ” L ” train or bus travel. You can buy these cards at the kiosks at the train stations. Click here to download the Ventra app and make your trip to Chicago a breeze.
Metra Rail
The Metra is a high-speed train that serves Chicagoland and the suburbs. You can find Metra Rail routes and fares here.
Ride Share & Taxi
You can flag down taxis all around the city. To request a ride you can use CHICABS, ARRO, and CURB. Credit cards are accepted in all taxis.
One of the cheaper ways to get around is via ride-sharing apps like Uber and Lyft.
Chicago Water Taxis
Two popular water taxis are the Chicago Water Taxi by Wendella Boats and the Shoreline Water Taxi by Shoreline Sightseeing. (My elementary school would often take field trips on Wendella Tours.)
Both companies are great choices for safe and fast ways to get to all the top tourist destinations around the City such as Chinatown, Museum Campus, Willis Tower, Michigan Avenue, Union Station, and Navy Pier. Tours on these Chicago Water Taxis are also included in the Chicago CityPass.
Driving
If you bring your car, here are some apps to help you find the cheapest and best parking.
- Interactive map of public parking facilities
- iParkit
- Millennium Garages
- ABM Parking
- ParkChicago
- SpotHero
- ParkWhiz
Chicago Cycling on Divvy
There are over 322 kilometers (200 miles) of protected bike lanes around the city. Chicago has a bike-share program called Divvy which offers over 580 stations and 5,800 bikes for rent 24/7.
Users pick up a bike from a self-service docking station and return it near their destination. You can find Divvy locations and rates here.
Chicago City Pass
The Chicago Explorer Pass is a great way to save money. The pass offers entrance to top attractions such as the Chicago Observation Deck, Field Museum, Adler Planetarium, and Lincoln Park Zoo.
You also have the option to choose activities, including a sightseeing cruise or hop-on hop-off bus tour.
When To Visit Chicago
Chicago in Winter From November to January
Christmas is an amazing time to visit for 3 days. While visiting Chicago for the weekend, check out the Christkindle Market. It’s modeled German Christmas markets so you can sip mulled wine, eat pretzels, and shop for Christmas gifts.
Christmas decorations on the Magnificent Mile are a feast for the eyes. Just be aware Chicago’s winters are brutal with the polar vortexes that come down and can reach sub-zero temperatures.
Chicago in Spring From March to May
March is rainy so bring your umbrella. Also, it’s tulip season so you’ll see all the beautiful buds sprouting along the Magnificent Mile. Temperatures around this time are from 4°C to 21°C (40 to 70°F).
March is a great time to visit Chicago during the annual dyeing green of the Chicago River for Saint Patrick’s Day. In addition, you’ll see beautiful cherry blossoms and experience the best weather in May. Just be aware Chicago’s weather is bipolar and it will be hot one day and cold the next.
Chicago in Summer From July To August
Chicago isn’t very humid. The perfect time to visit is during the summer months. Chicago has special events like the Taste of Chicago and Lollapalooza. Many people go to the beach during warmer months. Day temperatures reach 29°C (84°F) and at night, temperatures are 19°C (67°F).
Chicago in Autumn From September To October
Autumn is my absolute favorite time to be in Chicago. There are pumpkin patches out in the suburbs and the city comes alive with autumn and Halloween festivities. I highly recommend checking out Jack’s Pumpkin Pop-Up. During the day temperatures are around 18°C (65°F) and at night they drop to 10°C (50°F).
What To Eat in Chicago
I am a bit biased being from the Windy City; however, Chicago has the BEST food scene. I promise you will never go hungry in Chicago. Your choices include local Chicago specialties to cuisine from around the world. If you’re a foodie, welcome to heaven.
- Chicago Style Hot Dog – You can get one of these hot dogs at a Chicago favorite restaurant called Portillo’s. They’ll load your dog with mustard, relish, freshly chopped onions, sliced tomatoes, peppers, and a kosher pickle, nestled in a steamed poppy seed bun.
- Chicago Style Pizza – This is the most delicious diabetes on a plate. These pizzas are loaded with sausage, pepperoni, onions, peppers, mushrooms, and chunky tomato sauce, topped with mozzarella and romano. When visiting Chicago for the first time, try Uno Pizzeria & Grill, Gino’s East, Lou Malnati’s, and Giordano’s.
- Garrett’s Chicago Style Popcorn – Chicago-style popcorn is the perfect combination of savory hard cheddar and sweet caramel.
- Italian Beef Sandwich – Chicago has a huge Italian influence and you won’t get a tastier sandwich elsewhere. As for yours loaded with hot and sweet peppers and dipped in “gravy” (beef juice) for an unbelievably juicy, flavorful meal.
- Shaved Ice – Otherwise known as Italian ice, you can never go wrong with this cool and icy drink. During warmer weather months, cool off with a shaved ice at Mario’s Italian Lemonade, a mainstay stand since 1954, open May through September.
Popular Areas to Stay in Chicago
Choosing where to stay in Chicago can make a difference in your travel experience. Each neighborhood offers its own unique vibe and attractions, catering to different interests and preferences. Here are some of the best areas to consider for your stay:
Downtown Chicago (The Loop)
The Loop is the bustling heart of Chicago, making it a great place for first-time visitors. This area is home to some of the city’s most famous landmarks, including Millennium Park, the Art Institute of Chicago, and the Willis Tower.
You’ll be a short walk from major attractions, shopping on State Street, and the beautiful Grant Park. It’s the perfect central location for those who want to immerse themselves in the city’s energy.
River North
Just north of the Loop, River North has excellent nightlife, trendy restaurants, and eclectic art galleries. This area is perfect for travelers who want to enjoy Chicago’s dining and entertainment scene. Plus, you’ll be close to the Magnificent Mile (aka Mag Mile), offering luxury shopping and stunning views of the Chicago River. It’s also close to the Museum of Contemporary Art.
Gold Coast
Okay. So you’re bougie. Excellent. If luxury and elegance are what you seek, the Gold Coast is your go-to neighborhood. This upscale area boasts historic mansions, high-end boutiques, and the serene Oak Street Beach.
Staying here provides a quieter, more refined experience while staying close to the action. The Gold Coast is perfect for travelers who appreciate the finer things in life.
West Loop
I grew up close to the West Loop before it was gentrified to hell. And I’m not mad about its culinary delights…especially since the West Loop is a foodie’s paradise. You will also find Little Italy close by. This neighborhood is the best place for chic restaurants, hip bars, and boutique hotels.
Lincoln Park
Lincoln Park is an ideal choice for travelers who enjoy urban living and green spaces. This neighborhood offers the Lincoln Park Zoo and easy access to Lake Michigan. It’s perfect for travelers who enjoy outdoor activities and a more relaxed environment. Lincoln Park combines the best of city and nature, providing a refreshing escape within the urban landscape.
Hyde Park
Located on the South Side, Hyde Park is home to the prestigious University of Chicago and the fascinating Museum of Science and Industry. It’s also near the White Sox home stadium, Soldier Field. Hyde Park is great for travelers who want to explore Chicago’s rich academic and cultural history.
Recommended Hotels
When it comes to finding the perfect place to stay in Chicago, several standout options cater to different preferences and budgets. Here are some of the best hotels that will make your stay comfortable and memorable:
Luxury Hotels in Chicago
- Loews Chicago Hotel – Located in the heart of downtown Chicago, the Loews Chicago Hotel offers luxury accommodations with gorgeous lake views and floor-to-ceiling windows. Its central location provides easy access to Millenium Park, Navy Pier, and the Magnificent Mile, making it a top choice for first-time visitors.
- Hampton Inn Chicago Downtown – This hotel offers modern amenities, free WiFi, and friendly staff, ensuring a pleasant experience. It’s conveniently located near popular attractions and public transportation.
- Hilton Garden Inn by The Riverwalk – The Hilton Garden Inn is perfect for easy access to the city’s major attractions. It’s within walking distance of the Chicago River, Ohio Street Beach, and some of the best restaurants and coffee shops.
- Trump International Hotel – For those desiring a luxurious stay, you’ll enjoy over-the-top hotel rooms with panoramic views. Its prime location near the Chicago River and the Theatre District makes it ideal for exploring the city’s vibrant cultural scene.
Mid-Range Hotels in Chicago
- The Intercontinental Chicago Magnificent Mile – Located on Michigan Avenue’s Magnificent Mile, this historic luxury hotel is located in the city center with renowned on-site restaurants and an indoor pool.
- The LondonHouse Chicago – Sitting on Michigan Avenue and the Chicago River in a historic landmark building, LondonHouse features Chicago’s only tri-level rooftop bar with amazing city views. The hotel is less than a 10-minute walk from Millennium Park.
- Hotel EMC2 Chicago – Located alongside the shopping, dining, and entertainment of the famed Magnificent Mile, this boutique hotel is located in downtown Chicago. They have on-site dining, free wireless internet, and an expansive meeting space.
Budget Hotels in Chicago
- Virgin Hotels Chicago – This downtown Chicago boutique hotel combines modern luxury and comfort. They offer comfortable stays featuring an on-site restaurant, a rooftop bar, and nightclub.
- Millennium Knickerbocker Chicago – Located along the Magnificent Mile, this 4-star luxury hotel sits within one of the city’s historic tallest buildings. They offer unique dining options, a 24-hour fitness center, and well-appointed guest rooms.
- The Whitehall Hotel – A 4-minute walk away from the famous shopping, dining, and entertainment on the Magnificent Mile, this boutique hotel offers luxury and historic culture with upscale on-site dining and spacious guest rooms with free WiFi.
Chicago Hostel
Solo travelers and budget-conscious adventurers will find Chicago’s hostels a great option. Many hostels are in close proximity to the downtown area or the city’s main attractions. These are the places I recommend:
- Chicago Getaway Hostel – This hostel has a sun terrace, a garden with a picnic area, and a shared kitchen. If you choose a private room, you get additional amenities such as a dining table, a fridge, and a microwave.
- HI Chicago Hostel – This historic building offers a concierge service, a shared kitchen, a lounge, and a games room. Some units offer additional amenities such as a kitchenette, a work desk, and a private bathroom.
- Wrigley Hostel – This is an ideal place if you’re going to Wrigley Field for a Cubs game. It’s also close to the popular spot of Logan Square and the best bars up on the Northside.
Best Areas to Stay Based on Interests
Chicago’s diverse neighborhoods offer something for everyone, catering to a variety of interests and travel styles. Here’s a guide to help you choose the best area to stay based on your interests:
For Shopping Enthusiasts
If luxury shopping and high-end boutiques are your thing, staying near the Magnificent Mile and North Michigan Avenue is a must. This bustling area is home to some of the world’s most prestigious brands, including Louis Vuitton and countless department stores. It’s a shopper’s paradise, with everything from designer labels to trendy fashion finds, all within walking distance.
For Foodies
The West Loop and River North are culinary hotspots for food lovers. The West Loop, particularly around Randolph Street (known as Restaurant Row) has Michelin-starred restaurants and cozy bistros. River North offers a dynamic mix of trendy restaurants, chic bars, and coffee shops, making it perfect for those who love to explore new flavors. Hockey fans will love that it is near the United Center.
For Nightlife
If you’re looking to experience Chicago’s vivacious nightlife, Wicker Park and River North are the places to be. Wicker Park has a hipster vibe, with numerous bars, live music venues, and eclectic eateries. River North is equally lively, offering a variety of nightclubs, lounges, and entertainment options that ensure your evenings are just as exciting as your days.
For awesome live entertainment, I recommend checking out the Green Mill Cocktail Lounge. This former speakeasy is one of the most famous live music venues because it is longest continuously running jazz club in the country.
For History and Culture Buffs
History and culture enthusiasts should consider staying in The Loop or Hyde Park. The Loop is home to major cultural attractions like the Art Institute of Chicago, the Chicago Theatre, and the historic architecture of the Chicago Riverwalk. Hyde Park, on the other hand, offers a quieter but equally enriching experience with the University of Chicago, the Museum of Science and Industry, and a rich academic atmosphere.
For Outdoor Lovers
Lincoln Park offers beautiful parks, the Lincoln Park Zoo, and easy access to Lake Michigan. It’s perfect for morning jogs, strolls, or picnics by the water. The South Loop provides proximity to the museum campus, including the Field Museum and Shedd Aquarium, as well as Grant Park, known as “Chicago’s front yard.”
Tips for First-Time Visitors To Chicago
Welcome to your first adventure in the Windy City! Chicago is a city full of exciting experiences, and as your travel-savvy big sister, I’m here to make sure your trip is as smooth and enjoyable as possible. Here are some essential tips for first-time visitors:
Choosing the Right Area
Selecting the right neighborhood to stay in is crucial. Consider your interests and travel style when choosing your accommodation. Whether you’re a foodie, a history buff, or a shopaholic, Chicago has a neighborhood that’s perfect for you.
Using Public Transportation
Chicago’s extensive public transportation system, including the iconic “L” trains and buses, makes it easy to get around the city. Grab a Ventra card for convenient access to public transit and save on parking fees. The Blue Line, for example, offers a direct route from O’Hare International Airport to downtown.
Safety Tips
While downtown is generally safe, it’s always wise to stay aware of your surroundings, especially at night. Stick to well-lit, populated areas and avoid using your phone while walking. If you’re traveling solo, let a good friend or family member know your itinerary.
Packing Essentials
Pack comfortable walking shoes, as you’ll be doing a lot of exploring. Chicago weather can be unpredictable, so layers are your friend. Don’t forget a good travel bag to carry your essentials as you explore the city’s main attractions.
Plan Ahead
Make a list of must-see attractions like Millennium Park, the Art Institute of Chicago, and the Shedd Aquarium. I recommend the Chicago CityPass for booking tickets in advance to popular spots.
Embrace the Local Culture
Chicagoans are known for their friendliness. And from experience, I’ll tell ya we’re a lot nicer than New Yorkers. Don’t hesitate to ask locals for recommendations on the best places to eat, shop, and explore. If there’s one thing we love, it’s to share what we love most about the City. You might discover hidden gems that aren’t in the guidebooks.
Chicago is a city that truly has something for everyone, and knowing the right place to stay will significantly enhance your experience. From the bustling energy of The Loop and River North to the luxurious charm of the Gold Coast and the culinary delights of the West Loop, there’s a perfect spot for every type of traveler.
Whether you’re seeking luxury, budget-friendly options, or unique boutique hotels, Chicago’s diverse accommodations will ensure a comfortable and memorable stay. As you explore the Windy City, remember to embrace its vibrant culture, savor its incredible food, and enjoy its stunning architecture and attractions. Safe travels, and enjoy your adventure in Chicago!
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