Chicago is a vibrant city with so much to do, so much to see, and many ways to fill your time. Whether you dine at one of the many Michelin rated restaurants, catch a show downtown, or simply walk along the river, you certainly won’t have a dull moment on your trip to Chicago. If you can brave the cold, and a bit of a wind chill, then Chicago is an amazing city to visit with so much to discover. There are many things to consider before visiting any new place, check out my top things to know before visiting Chicago to make the most of your trip.
1. Transportation & Accessibility
Clean, walkable, and easy to get around, Chicago is a very tourist friendly city. This is a pretty big deal when traveling, transportation to and from each place can make the difference between spending your time navigating the city, or walking around and enjoying the sights. It’s important to note Chicago’s clever layout, with streets divided north and south of Madison, and eight blocks to every mile. With charming bridges, commanding buildings, and clean walkways all lining your way, Chicago is beautiful and easy to walk from place to place and all you have to do is pay attention to the street sign. Taxi’s, Uber and public buses are all alternative and convenient options for getting around. If you venture more into small towns in Chicago, those are a fun place to visit as well and car rentals would be great for this. I visited Naperville while I was there, which made the list as one of the best small towns to live in America. Quaint, safe and cozy, this little town added to the charm and appeal of Chicago even beyond the glittering reputation of the city.
2. Things to Do
With an estimated 2,695,598 people living in Chicago, there has got to be man ways to feed, clothe and entertain these folks. Within Chicago’s 237 square miles of land exists more than 200 theaters, almost 200 art galleries, over 7,300 restaurants, as well as dozens of cultural institutions, historical sites, and museums. For those wanting to shop, there are lines of high end stores to spend your travel allowance, or window shop at all the glam. For those who simply enjoy strolling, and a good walk, the Chicago riverwalk is a popular spot for an open, pedestrian-friendly stroll along South bank of the Chicago River in downtown Chicago. This walk will keep you busy for a few hours, as it spans from Lake Shore Drive to Franklin Street. There are many other great bridges along the way as well for those exploring by foot. Live entertainment, delicious dining, tons of live entertainment, bars and nightlife are definitely a theme when visiting Chicago.
3. Accommodation & Where to Stay
Chicago has over 77 neighborhoods, each with their own flavor and personality, as well as restaurants, sights, attractions, and locals. Before booking your trip, decide what vibe you’re going for, and book it accordingly. Look up the stats on the areas to make sure it’s safe, especially if you’re renting someone’s home through Airbnb or VRBO. Look up the address and map of the location to make sure it’s accessible to what you want to see in Chicago. I stayed in Trump hotel, and it was extremely accessible to downtown and nightlife. It gave me the “in the city” experience I wanted. Make sure you research thoroughly before booking anywhere and give yourself a few weeks in advance to book to make sure all the best deals are available and the best spots aren’t taken, especially during the bustling holiday months.
4. When To Visit & Weather Considerations
As with any destination, it’s imperative that you look up the weather before planning your trip. I visited Chicago in early to mid-December. The weather was certainly cold, the ground and trees were covered in snow. Even for those who “can’t stand the cold”, as long as you are properly dressed, the cold is not an issue and the white accents on the city from the snow just adds to Chicago’s charm in the winter. With so many people living in the city year round, there are events to check out any time of year. Chicago is a 4-season state, so pick your preference on which is your favorite, and be assured that you will find fresh buds in the spring, heat in the summer, vibrantly colored trees in the fall, and snow in the winter.
Spring: Chicago’s many lakes and rivers will be lined in blooming flowers and active Chicago residents strolling along the waterfront. With weather ranging around 50-60 degrees and up to 70 in May, the snow has melted and this is a great time to visit.
Summer: Lows of 77 and highs of 92 are the norm for Chicago in the Summer months. Chicago witnesses many summer showers, though, June being the wettest month of the year.
Fall: Vibrant leaves and a temperature ranging from 70 degrees, dropping down to the mid-40s as it gets later in the year. If you’re not much for the rain, visit in October, Chicago’s driest month of the year.
Winter: Averages 37 inches in annual snowfall, temperatures range from 30-38 degrees, and there is a ton of winter-themed activities. Oversized Christmas trees, decorated streets, shops, and restaurants are a testament to Chicago’s holiday spirit.