7 Tips & Tricks | Traveling to Chicago for the First Time

A city so nice we built it twice — Chicago. While it may or may not have been set ablaze by a cow tipping over a lantern, Chicago’s story is undoubtedly a unique one. Rife with mafiosos, political corruption, and all the salacious stories from Prohibition, the city has a lot of tales to tell. When it’s your first time in Chicago, it might be intimidating to approach your adventure and go home feeling like you did it all. 

You won’t be able to do it all in a few days on your first trip. But I can help you feel like you’ve gotten a worthwhile experience out of my favorite city. Take it from a small town to Chicago transplant; the big city isn’t big and scary. 

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1. Stay for a few days

I cannot tell you how many people have said to me, “I can’t believe how big Chicago is,” on their first trip to Chicago. Even though we’re the third largest city in the United States, people tend to underestimate the Windy City. We don’t have Times Square or the Hollywood Sign, though we’re iconic in our ways. That’s why you want to have at least a few days to enjoy the city. 

Even if you don’t venture far out of downtown, there is still so much to do, even on a two-day itinerary in Chicago. When you try cramming all the big Chicago attractions into one day, you aren’t getting a great experience. What you get instead is a headache. Give yourself a few days to explore the city without running yourself ragged. 

Three to four days is a reasonable amount of time for a first trip to Chicago. You get a taste of the city without making a significant commitment. Plus you’ll have plenty to come back and see on your return visit. 

Sightseeing boat with tourists on the Chicago river in the Chicago Loop in Chicago. The Loop is one of Chicago district and the seat of Chicago's government.

2. Consider visiting during shoulder season

Chicago in the summer is a tourist hot spot. If you ever Google the best time to travel to Chicago though, you’ll be directed to the shoulder season. We’re talking late spring or early fall. When the tulips along the Magnificent Mile are in full bloom or the trees are embracing their autumnal hues. 

Our Midwestern location might trick you into thinking summertime isn’t so bad, but I’m here to tell you it is. High humidity makes it harder for your sweat to evaporate which makes you feel hotter. So even if the average summer temps in Chicago are in the 80s, it often feels much worse. 

A bonus to visiting in the shoulder season is that not as many tourists are here. Other than the weather, that’s why it’s the best time to visit Chicago. You won’t have to deal with the unrelenting summer heat, there’s fewer crowds, and you’ll save money on things like accommodations or tours. That’s a win-win! 

3. Stay Downtown for easy access

Many Chicagoans don’t spend a lot of time downtown simply because there are 76 other neighborhoods besides The Loop – and many of us live there. Still, when you’re wondering where to stay in Chicago, downtown is an obvious choice. 

You don’t have to go far to enjoy anything from my beloved deep dish pizza to The Bean over at Millennium Park, a lot of our major spots are walkable in downtown. Not to mention that many of my favorite city hotels are downtown. 

Chicago skyline panorama with skyscrapers and Buckingham fountain in Grant Park at night lit by colorful lights.

4. Mix it up between big tourist attractions and lesser-knowns

Anyone who has seen a John Hughes movie (a native Chicagolander) knows that there’s a lot going on here. There are always exciting things to do in Chicago and many of our heavy hitters are known worldwide. We’re home to one of the world’s best art museums (the Art Institute of Chicago), one of the largest natural history museums (the Field Museum), and the once tallest building Willis Tower (formerly Sears Tower). 

When you’ve got mini amusement parks and shopping adventures at Navy Pier or cheering on the White Sox, it’s hard to justify making room for other activities. But you don’t even need to leave downtown Chicago to enjoy things like touring the gorgeous Chicago Cultural Center with its Tiffany glass dome or marvel at Frank Lloyd Wright’s Rookery Building. Both of those spots are free and will only take a little time to appreciate. 

Even if you’re splitting your time between observation decks or the museums and our favorite lesser-known spots, I still recommend investing in a Chicago CityPass. One payment for the pass will get you into a bunch of our attractions at a fraction of the cost if you bought tickets at the door. 

5. Save your feet and take the L

Look, Chicago public transportation isn’t perfect. That said, it is super convenient for hopping around the city. Like in Manhattan you could walk all over without stepping foot on the L (elevated train) or subway – but your feet will hate you for it. You can buy a weekend or multi-day transit pass to save money. 

A few pro-tips for transit in a big city: 

  • Never board an empty train car – there’s a reason it’s empty.
  • Keep your belongings with you, not on the ground or a seat by you.
  • If you are seated in a full car without available seats and an elderly person, disabled person, or mother with young kids gets on the train, let them have your seat. 
  • Don’t smoke or vape on the train. Yes, marijuana is legal here but hotboxing the other passengers isn’t cool. 
Chicago Board of Trade Building along La Salle street in Chicago Illinois. The art deco building was built in 1930 and first designated a Chicago Landmark on May 4 1977.

6. Eat the Chicago foods but try other things too

Far be it from me to tell a visitor not to try Chicago foods. Comfort staples like a Chicago style hot dog, Italian beef, and deep dish are quintessentially Chicago. Yet these tasty treats are not the only cuisine on the menu. 

For those seeking a higher cuisine experience, Chicago is home to 21 Michelin-starred restaurants. We are even home to two Michelin three-starred restaurants: Alinea and Smyth. There are also currently 47 Bib Gourmand restaurants in Chicago. A Bib Gourmand is a title bestowed by Michelin recognizing restaurants that serve excellent food that is well priced for diners. 

At the opposite end of the spectrum you have the best tourist restaurants in Chicago. Those are your fast foodie joints like Portilllo’s and Giordano’s which are great for a filling lunch or dinner. I absolutely endorse eating at the massive Eataly location in River North or taking in the sunset at LondonHouse’s rooftop bar. These places are staples for good reason. 

Otherwise if you want some local favorites and are willing to venture out of downtown, we won’t let you down there either. You could pop over to Girl & the Goat in the Fulton Market neighborhood on the West Side or Little Bad Wolf in Andersonville on the North Side. As you can see, we’re a foodie city for a reason. 

Homemade Skillet Deep Dish Chicago Pizza with Mozzarella

7. Don’t be afraid of Chicago or Chicagoans

Sometimes when visitors come into the city, they might have preconceived notions of city dwelling people. We might hustle down the sidewalk faster or neglect to make polite conversation with strangers, but it doesn’t mean we’re scary. We’ll happily give you directions if we can (and aren’t running late for something). 

Chicago might be one of America’s largest cities, but it still very much entrenched in Midwestern niceness. 

Chicago also has an inaccurate reputation for being really dangerous. It’s a topic I’ve written about a lot. So I know the reputation is pervasive for travelers. I want you to know, from a person who grew up in a one main street town, that Chicago is just another big city. Neighborhoods in big cities especially will have an uptick in crime because of population, increased poverty and a slew of bias related issues. Unfortunately, that’s just how crime data works. 

The fact is, crime happens everywhere. When you have more people in a place, it will statistically happen more often. That doesn’t mean you should never visit a place. We want you to come see how magnificent Chicago is. And I want to help you feel as safe as you can. 

Here are some tips from a chronically anxious human like me to make you feel empowered to experience Chicago at its best: 

  • Bring an umbrella! Midwestern weather is super unpredictable. Even if there is no chance it will rain (or snow) when you visit, it’s still possible. 
  • Don’t engage with anyone trying to hand you anything. Even if it’s a random man dressed as a monk, it’s a scam. 
  • Be aware of your surroundings and keep your head up, not buried in your phone or conversation. 
  • Keep your wallet and phone in a front pocket. 
  • Follow pedestrian traffic signs and don’t jay walk. 
  • Avoid walking by yourself at night. 
  • Never, ever, ever try swimming in the Chicago River. It’s super dangerous and contaminated
  • If a stranger offers you a ride in an unmarked car like an unlicensed cab at the airport, say no. 

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  • Amanda Finn

    Amanda, a Chicago-based travel journalist, has explored 20 countries and 27 states since childhood. Featured in publications like Huffington Post and Ms. Magazine, they specialize in LGBTQIA+ travel, theme parks, itineraries, traveling with pets, and purposeful travel.

    View all posts https://www.tiktok.com/@finnwrites

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