Chicago Travel Guide 2026

Published on November 26, 2024 · Written by Zack Fenech

Top Travel Resources for Chicago

My then-girlfriend, now wife, always told me how much she wanted to visit Chicago one day. So, you can imagine her unbridled excitement when I told her we’d be spending New Year’s in the Windy City.

I’ll admit that I was nervous about visiting the third-largest city in the United States. After all, it has an unvarnished relationship with crime, evident in history, music, and the news cycle.

But the moment I left Chicago, I missed it. It wasn’t a city where you could let your guard down, but I loved every minute of the four days I was a Chicagoan.

While we decided to visit the Windy City for New Year’s Eve, this Chicago travel guide focuses on tips and insights that will make your visit fulfilling, no matter what time of year you decide to go. For more destinations in the country, check out our USA travel guide.

Essential Things to Know Before Visiting Chicago, Illinois

Airports

Use Skyscanner to find and compare the best flights to Chicago. The city has two airports: O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Both have a subway station leading to the city centre – ORD’s station is the first stop on the Blue Line, while MDW’s Midway station is the first on the Orange Line.

Transportation

One of Chicago’s most noticeable features is its public transportation system, known affectionately as the “L” – a colloquial name denoting the elevated train. To ride transit, visitors must purchase Ventra cards for USD $3.50 per fare, which lasts two hours after activation. Your best bet is to purchase a day pass for USD $5, active for 24 hours after your first tap. Uber and Lyft are also available throughout the city.

Health and Safety

Be sure to get travel insurance before your trip. The emergency number in Chicago is 911. While Chicago has a well-documented issue with crime, don’t let this deter you from visiting. The city’s dangerous areas are not close to any of the points of interest in this guide. Avoid West Garfield Park, East Garfield Park, Fuller Park, Washington Park, and parts of South Side Chicago.

Currency and Tipping

Chicago uses USD. Many independent restaurants and bars are cash only. Tipping culture is firmly in place here, with 18% being the norm.

Walkability

Chicago is a very walkable city, though many neighbourhoods of interest are spread apart, meaning you’ll need to rely on transit between some areas.

Weather

Chicago is best visited in the spring, summer, or autumn. While we visited in winter and didn’t experience any truly frigid days, the city is undoubtedly best experienced with fairer weather.

Best Areas to Stay in Chicago

Chicago’s nicest neighbourhoods will have you looking at properties on Zillow more than once. Below, I’ve outlined some of the best areas to stay. For the best deals on places to stay, book hotels online ahead of your visit.

Lincoln Park

A more upscale area, Lincoln Park is one of the most beautiful places to visit and stay in Chicago. It is safe and within walking distance of the downtown core, surrounded by beautiful urban greenery and notable points of interest like the Lincoln Park Zoo, Diversey Harbor, and Lake Michigan.

Wicker Park

One of Chicago’s trendiest areas, Wicker Park boasts small businesses, electrifying murals, and a great bar, restaurant, and nightlife scene – ideal for couples or younger visitors.

Logan Square

We stayed in Logan Square, another trendy neighbourhood with an unassuming vibe perfect for local artists, vintage shoppers, and those looking for an authentic local experience.

Old Town

Perhaps Chicago’s most picturesque neighbourhood, Old Town’s charm lies in its rich history, cobblestone streets, beautiful old architecture, and famous comedy venues – Second City and Zanies Comedy Club both have locations here.

River North

Stay in River North and you’ll be near art galleries and high-end shopping along the Magnificent Mile.

West Loop

The West Loop is perfect for food lovers, offering world-class restaurants and chic bars in one of the city’s most exciting dining destinations.

Things to Do and Places to Visit in Chicago

Whether you’d like to visit all the major points of interest or simply admire the architecture from outside, Chicago has much to offer.

1. Downtown Chicago (Chicago Loop)

Downtown Chicago is where many start their trip, as it features some of the most iconic points of interest in the city, including the Magnificent Mile, the Art Institute of Chicago, Chicago Theatre, Millennium Park, Cloud Gate (The Bean), Navy Pier, and Marina City – all within walking distance of one another in one of the city’s safest and most bustling areas.

2. Lincoln Park

Lincoln Park is a massive park surrounded by upscale neighbourhoods with beautiful homes, restaurants, coffee shops, and bars. Inside the park there’s the Lincoln Park Zoo (free), Lincoln Park Conservatory (free), Chicago History Museum, North Avenue Beach, and Kingston Mines – a massive blues bar that was the highlight of our trip, offering 12 hours of live music on New Year’s Eve.

3. Old Town

Old Town features cobblestone streets lined with restaurants, coffee shops, boutique stores, and iconic comedy clubs. Must-visits include Second City (the legendary improv club that launched careers from Jim Belushi to Tina Fey), Zanies Comedy Club, and the Old Town Ale House – a historic dive bar called the best bar in the world by film critic Roger Ebert.

4. Wicker Park

If you’re into trendy, artsy neighbourhoods, look no further than Wicker Park. Home to vintage shops, great restaurants, and breweries, it’s a great place to spend a day shopping, grabbing coffee, and exploring the local bar scene.

5. Logan Square

Logan Square is another artsy neighbourhood with a vibe similar to Wicker Park. You’ll find unique boutiques, trendy restaurants, excellent breweries like Revolution Brewery, and music venues to catch local and touring acts. Rosa’s Lounge is highly recommended for a fantastic evening of blues music.

Food and Drink to Try in Chicago, Illinois

1. Deep Dish Pizza

Most Chicagoans don’t eat deep-dish pizza regularly, but you’d be missing out if you didn’t try it. Chicago deep dish has cheese in a thick, deep crust beneath the sauce. Two places worth visiting are Pequod’s and Pizzeria Uno – the latter is where the dish originated over 80 years ago.

2. Chicago-Style Hot Dog

A Vienna sausage on a poppy seed bun, topped with yellow mustard, relish, tomatoes, pickles, peppers, and celery salt. Note: Placing ketchup on a Chicago-style hot dog is a major faux pas. Try Red Hot Ranch in Bucktown or The Wiener’s Circle in Lincoln Park.

3. Italian Beef Sandwich

One of the greasiest and most delicious meals I’ve ever eaten. Served on a roll with thinly sliced beef and Italian peppers, you can order it “wet” (submerged in beef juice) or “dry.” We visited Mr. Beef in the Chicago Loop – the restaurant the FX show The Bear is set in, open since 1979.

4. Chicago Popcorn (Chicago Mix)

Chicago Style Popcorn combines caramel popcorn and cheddar cheese for a sweet-and-savoury snack. Created by Garrett Popcorn Shops, which has locations all over the city.

5. Malort

Malort is a bitter liqueur originally brought to Chicago by Swedish immigrants. It’s awful and a rite of passage among Chicagoans. Try a shot at the Old Town Ale House and add it to your list of regrets.

My Final Thoughts: Is Chicago Worth Visiting?

Chicago is a beautiful city, and the reason is simple: the architecture. It cannot be overstated. Walking across bridges to glimpse the skyline from different angles made the city feel meticulously designed – a landmark example of human achievement echoing through time. My only regret is not going in warmer months.

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