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Home » Blog » New to Chicago? Here’s What You Need to Know Before You Visit

New to Chicago? Here’s What You Need to Know Before You Visit

Admin By Admin July 16, 2025 12 Min Read
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New to Chicago? Here’s What You Need to Know Before You Visit

Are you planning to visit Chicago anytime soon? It’s an excellent idea, since the city holds many attractions in store for you.

Contents
Chicago 101: Where Is Everything and What’s Worth SeeingNeighborhood Vibes: Where to Stay Based on Your Travel StyleDon’t Let the Weather Surprise You: What to Pack for Any SeasonBeyond Deep-Dish: What (and Where) to Eat in ChicagoGetting Around: The CTA, Ubers, and Why You Might Just WalkThings You Can’t Miss: Iconic Attractions + Local FavoritesPlanning on a Budget? Here’s What You Can Do for Free (or Cheap)When to Visit Chicago (and When to Avoid It)Staying Short-Term? Why Serviced Apartments Are a Smart Choice

Chicago 101: Where Is Everything and What’s Worth Seeing

There’s the vibrant downtown zone called The Loop which houses several landmarks like the Millennium Park, Cloud Gate, and the Art Institute. You’ll love the Magnificent Mile, Navy Pier, Skydeck Chicago for stunning views, and a whole lot more here. 

Stimulate your mind at the Chicago Cultural Center and watch magical performances at the Chicago Theater. Explore the popular Lincoln Park with its zoo, museums, and other recreational choices. Take river tours, check out the fabulous parks, taste the fabulous deep dish pizza, and get a feel of ethnically diverse neighborhoods like Chinatown, Greektown, and Little Italy. Sounds exciting? Let’s check out everything you need to know, right from the top neighborhoods for vacation rentals in Chicago to attractions and a lot more. 

Neighborhood Vibes: Where to Stay Based on Your Travel Style

You’ll find several holiday rentals Chicago in some of the hippest neighborhoods. There’s something to match every travel style and preference. Let’s take a closer look at them below.

  • River North– You’ll love this buzzing neighborhood with its abundance of nightlife choices, clubs, bars, restaurants, and more. There are several art galleries here as well. 
  • Lincoln Park– It is a more relaxed area with its park, zoo, conservatory, and the famous Chicago History Museum. You’ll love the multitude of shopping choices here along the Armitage Avenue. 
  • Pilsen– Falling love with Pilsen is a given! It’s got a bustling vibe with historic architectural wonders, Mexican-American flavors, and the imposing National Museum of Mexican Art. The local dining circuit is worth checking out here with several eateries and taquerias. Thalia Hall is also another landmark, hosting varied performances throughout the year. 

Don’t Let the Weather Surprise You: What to Pack for Any Season

One of the most important things to keep in mind while visiting Chicago is to stay prepared for almost any season. 

  • Don’t miss comfortable walking shoes and sunscreen along with a reusable water bottle to stay hydrated on your trip. 
  • Carry a light jacket and rain jacket along with an umbrella. 
  • You should also keep a swimsuit and a pair of gloves and hat for colder weather.
  • Pack layers since the weather can be unpredictable. Opt for long-sleeved shirts, t-shirts, coat, and sweaters. 
  • Have a daypack or tote bag to carry your essentials, along with travel-sized toiletries.

Beyond Deep-Dish: What (and Where) to Eat in Chicago

It’s not just about trying the signature deep dish Chicago pizza; there are multiple things to sample in the city along with several well-known eateries. Don’t miss the Chicago-style hot dog with its tempting beef frankfurter on a poppy seed bun and accompaniments like yellow mustard, bright green sweet pickle, white onions, dill pickle spears, tomatoes, and more. Other must-trys include the Maxwell Street Polish Sausage and the innovative Rainbow Cone with five unique flavors. 

Dine at Lou Malnati’s Pizzeria, The Original Rainbow Cone, Portillo’s, Kasama, and Harold’s Chicken for the best taste of Chicago. There are several underrated hidden gems in terms of neighborhoods that offer some of the best dishes and eateries worth trying. These include Pilsen, with its Mexican vibes and authentic taquerias and Bridgeport with its authentic Chinese eateries. Then there’s West Ridge that offers Indian, Pakistani, and Korean food, while Uptown is a hub for Thai, Vietnamese, Chinese, Caribbean, and Ethiopian food. Talk about diversity!

Getting Around: The CTA, Ubers, and Why You Might Just Walk

Getting around Chicago is never hard. You can use the CTA (Chicago Transit Authority) network with its buses and L train lines which are affordable too. While they are efficient, they may be slower while traveling outside the downtown zone. You can also download the CTA app for real-time bus and train updates. 

Uber and Lyft are also available although they can be costlier during peak hours. Use the Pair & Pay feature to pay for taxis with the Uber app during your trips. In fact, if you’re up for it, you can just walk instead. Explore Chicago at your own pace and find more hidden gems than you expected! So, you can use the CTA for traveling within the downtown area, walk to nearby landmarks, and use Lyft or Uber for longer trips outside downtown. 

Things You Can’t Miss: Iconic Attractions + Local Favorites

The Bean is undoubtedly cool, although have you ever thought of a unique river architecture tour or even a fun night at a jazz club? Chicago’s got tons of unique experiences in store for you! Some of them include the following: 

  • Millennium Park– This is where you’ll find the Bean or Cloud Gate along with the Lurie Garden, Crown Fountain, and tons of public spaces, art, and architecture. 
  • Art Institute of Chicago– You’ll love exploring this famous art museum with its vast collection. 
  • Skydeck Chicago, Willis Tower– How does seeing the city from the 103rd floor sound? Thrilling right? That’s the experience you’ll get when you reach this landmark. 
  • 360 Chicago– This one also gives you another fascinating view of the city from the 94th floor deck. You can also enjoy the TILT (moving glass platform) experience to the hilt!
  • Navy Pier– It’s one of the most vibrant entertainment zones with several restaurants, shops, amusement rides, and gorgeous views of Lake Michigan. 
  • Chicago Riverwalk– hop onto a boat and meander along the Chicago River, getting magnificent glimpses of the architectural marvels of the city. 
  • Magnificent Mile– This one is as groovy as it gets! You’ll fall in love with the fabulous shopping experiences on offer here, courtesy of the boutiques, department stores, and premier retailers. 
  • Chicago Theater– It’s an awe-inspiring marvel with its historic legacy and fabulous Broadway and other performances. 
  • Museum Campus– You should not miss exploring this campus which houses the Shedd Aquarium, Field Museum, and the Adler Planetarium. 
  • Garfield Park Conservatory- Escape into a lush green sanctuary filled with exotic plants and beautiful landscapes. 
  • Museum of Science and Industry– From interactive exhibits to fabulous scientific and technical offerings, this museum will bowl you over instantly. 
  • Lincoln Park Zoo– How about indulging in a day of viewing spectacular wildlife? You can explore this free zoo with its lovely gardens and diverse animal species.

Of course, you can also venture beyond the touristy circuit and check out some hidden wonders like Chinatown, Wicker Park, Pilsen, and the Chicago Cultural Center with its cultural events and stained-glass windows.

Planning on a Budget? Here’s What You Can Do for Free (or Cheap)

If you’re planning to visit Chicago on a budget, there are several affordable yet free things that you can do easily in the city. These include the following: 

  • Check out the public art in the city with its murals and sculptures and explore the parks for a soothing experience.
  • There are several free festivals happening in Chicago throughout the year, especially in the summer. 
  • Free museums and landmarks include the amazing Lincoln Park Zoo, National Museum of Mexican Art, Museum of Contemporary Photography, and the Chicago Cultural Center. 
  • Several museums also offer free days, including the Adler Planetarium, Shedd Aquarium, Art Institute of Chicago, and the Museum of Science and Industry.
  • You can also embark on free walking tours to view the eclectic localities and stunning architecture. 
  • Walk along the Lakefront Trail and explore the Riverwalk, while visiting the Millennium Park with its famous Bean sculpture.
  • You can also explore Chinatown and the Navy Pier for vibrant experiences. 

When to Visit Chicago (and When to Avoid It)

The best time to visit Chicago is in the spring, between April and May. You can also consider visiting during the fall (September to October) for lovely weather and lesser crowds in comparison to the peak season, which is summer (June to August). The latter period is undoubtedly the most crowded, with its warm weather, festivals, outdoor attractions, and more. However, it can also be costlier in terms of finding furnished housing Chicago for short or long-term stays and also with regard to airfares. 

Spring or fall may be slightly more affordable in comparison to the summer rates. Winter (November to March) can be snowy and chilly, although you’ll find several deals on accommodation and flights at this time. Chicago also has a packed yearly calendar and you can look up festivals, events, and other concerts in order to plan your trip around them. If you love festivals and outdoor activities and don’t mind the crowds, consider the summer. Conversely, if a relaxed pace and lower prices are what attract you, fall or spring are the best options. 

Staying Short-Term? Why Serviced Apartments Are a Smart Choice

If you’re looking to put up in Chicago for the short term, serviced apartments are an excellent option. They offer more space and privacy in comparison to regular hotels, while offering attractive rates for extended stays. You can also expect flexible lease terms and great hotel-like amenities fused with home-like comfort. At the same time, you’ll find everything from Wi-Fi and work desks to appliances, well-equipped kitchens, flat-screen televisions, receptions, concierge services, and a lot more.

Before booking, check for pet friendly vacation rentals Chicago if you’re looking to travel with your furry friend. At the same time, compare locations, pricing, amenities, and the interior designs before you finalize your decision. TheSqua.re is also an excellent option to find apartments to your liking in Chicago spanning prime locations, verified listings, reasonable rates, and of course, great amenities.

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