Chicago, the Windy City, famous for its skyscrapers, the iconic Bean, and the river cutting through its heart, completely surprised me… even in the middle of winter! I found it elegant, refined, and incredibly clean. After chatting with friends, we all agreed on one thing: Chicago never leaves anyone indifferent. Its energy pulls you in, and in this article, I’ll show you exactly why. Here you’ll find the best things to do in Chicagothe best time to visit, the top areas to stay, and my best budget travel tips to enjoy the city without breaking the bank.

In this guide, I’ll show you what to see in Chicago, the best time to visit, where to stay without breaking the bank, and how to get around the city hassle-free. All with reliable information and practical tips to make your trip unforgettable.

When to visit Chicago?

Chicago has something to offer in every season, but some times of the year are more recommended than others.

• Winter (January-February): Temperatures are extremely cold, the wind can be relentless, and the city has lost the holiday magic. If you don’t mind the extreme cold, you can enjoy seeing the city almost empty and take advantage of lower accommodation prices.

• March: ideal if you want to experience St. Patrick’s Day, which is celebrated in a big way. They even dye the Chicago River green! A unique and highly photogenic experience.

• Spring: the days start getting longer, but they are often rainy and cloudy. Still, the parks and gardens begin to bloom, adding a beautiful splash of color to the city.

• Summer: warm and lively, perfect for enjoying outdoor festivals, urban beaches, and river activities. Keep in mind, it’s high season, so accommodation prices go up and it’s best to book everything in advance.

• Autumn: the best time to visit Chicago according to many travelers. The weather is milder, the colors in the parks are spectacular, and you can enjoy the city without the summer crowds.

Where to sleep in Chicago?

If you’re wondering where to stay in Chicago, the top neighborhood is The Loop: central, full of iconic skyscrapers, and with easy access to many attractions. But keep in mind: once business hours are over, The Loop goes quiet until the next morning.

If nightlife is important to you, it might be better to look for accommodation a bit further north, in neighborhoods like River North, known for its bars, restaurants, and lively party scene.

Another hipster and alternative option is Wicker Park, a neighborhood filled with coffee shops, art galleries, and a creative atmosphere that lets you experience the more authentic side of Chicago.

💡 Heartfelt Recommendations

:

• High budget: The Peninsula looks amazing, and Nobu Hotel is on my wish list.
• Mid-range budget: Staypineapple is spectacular, and I’ve heard great things about Arlo Chicago.
• Budget-friendly: Hi Hostel has a great location, and I love the décor at Freehand.

How to Get From Chicago Airports to Downtown

If you arrive at Chicago O’Hare International Airport (ORD)—one of the busiest airports in the U.S.—it is located about 27 km (17 miles) from downtown Chicago.

The CTA Blue Line connects O’Hare Airport directly to downtown Chicago. You need to go underground from Terminals 2 and 3. A ticket costs $5 USD and can be paid with cash, card, or Apple Pay. The ride takes about 45 minutes to reach the city center.

15 things to do in Chicago

Here are my 15 must-see attractions, perfect for travelers on a budget who still want to experience the city to the fullest:

1- Free walking tour around Chicago:

As I always recommend, the best way to discover a new city and understand its history, neighborhoods, and architecture is by taking a guided tour. Chicago’s history is spectacular: the Great Fire of 1871, its reconstruction, and its infamous mafia past led by Al Capone. Free tours are an excellent option for budget travelers, as you only pay the tip you consider fair at the end (always take into account the cost of living of the city you visit—around $15–20 USD minimum for Chicago).

If you’re mainly interested in the city’s criminal past, then this tour is for you.

2- Chicago Riverwalk

Walking path that follows the Chicago River, perfect for enjoying the city’s skyline. Along the route, you’ll find green spaces, cafés, and restaurants—ideal for taking a break and soaking up the atmosphere. Additionally, closer to the riverbank, there are quieter, less touristy areas right in the heart of downtown.

3- Walk around The Magnificent Mile (Michigan Ave)

It is often compared to New York’s Fifth Avenue. Perfect for strolling, browsing luxury shops, admiring impressive buildings, and enjoying great restaurants. The area is always bustling with people and activity—ideal for capturing the vibrant essence of Chicago.

4- Try Garrett's popcorns

If there’s one thing you can’t miss in Chicago, it’s Garrett Popcorn. This chain has several locations throughout the city and offers many varieties, but I recommend trying the Garrett Mix, which perfectly combines sweet and salty: half caramel, half cheddar cheese. They come in three sizes, and besides being a delicious snack, it can also be a fun souvenir to take home. Yes, I fell for the hype—and you should too.

5- Millennium Park y Grant Park

Millennium Park is located within Grant Park and, currently featuring three main attractions, is one of the most visited spots in Chicago. Here you’ll find:

-> Cloud Gate, also known as The Bean. It is a structure made of stainless steel plates that reflect and distort the surroundings. Nowadays, it’s the most photographed landmark in Chicago.

-> Crown Fountain is a rectangular concrete plaza featuring two pillars that display various faces, with water jets that appear to come from their mouths. It’s not my favorite, but it’s a curious, tech-inspired attraction and very close to the other highlights.

-> Jay Pritzker Pavilion is a venue that hosts a wide variety of concerts in Chicago. Visiting in winter, I wasn’t lucky enough to attend any, but its architecture and design still make it worth seeing.

6- 360° Observation Deck

Located near Michigan Avenue, it offers 360° views of the city and the lakefront. Before reaching the top floor, the tour includes an introduction to Chicago’s neighborhoods, showing a map with their boundaries, historical data, and key characteristics of each area. I found it very interesting.

Once at the top, you’ll find enclosed viewing areas and an outdoor section called “Walk the Sky,” with no glass barriers. You can feel the wind, hear the sounds of the city, and experience Chicago in all its glory.

The ticket costs 30 USD, with an additional 9-10 USD for the TILT experience, which makes this observation deck unique. For three minutes, a window tilts, giving you the feeling of being suspended in the air 94 floors above the city—an unforgettable sensation.

7- See the Chicago Skyline from Museum Campus

Chicago doesn’t just shine for its museums; it also offers incredible outdoor views. Museum Campus is a park and promenade along Lake Michigan that allows you to see much of the city skyline, including the iconic Willis Tower.

I visited on an extremely cold and foggy night, so the photos don’t do it justice. Even so, walking through this open space, with the fresh air and the view of illuminated skyscrapers, is one of the most authentic Chicago experiences.

8- Visit Wrigleyville, specifically Clark Street

For those looking for nightlife, bars, and good food, Wrigleyville in the north of the city is fantastic. The famous Clark Street is full of charming bars and restaurants, where you can enjoy the authentic Chicago nightlife.

We traveled in October and chose Baby Santa Bar, and I fell in love! Every corner was full of details, lights, and decorations that make the experience unique. I recommend checking the Chicago Highlights on @guadiviajando (way back, haha) to watch the videos and feel a bit of the magic of the place.

9- Eat Dish Deep Pizza (sooo yummy)

Literally, before the Bean, when I think of Chicago, the first thing that comes to mind is its deep-dish pizza. It’s a thick pizza, baked in a deep pan, loaded with cheese, and topped with sauce and other ingredients. The most famous are Lou Malnati’s and Giordano’s, and my most sincere recommendation is the latter.

At Giordano’s, there’s usually a waiting list (we waited about 30 minutes), but it’s so well organized that you can join the list and place your order while you wait. They take your phone number and notify you by message when your table is ready. A small pizza, perfect for 2 to 3 people, costs around 19 USD.

Giordano’s now has numerous locations across the U.S., so you can try it in other cities as well.

10- Navy Pier

Es un muelle icónico de Chicago, que en su momento funcionaba como puerto y tuvo un papel importante durante la World’s Columbian Exposition, cuando la ciudad se abrió al mundo.

Today, it’s a promenade with an amusement park, restaurants, and a huge Ferris wheel offering views of Lake Michigan. The concept and the views are really nice, but to be honest… the park itself leaves a lot to be desired compared to all the amazing things Chicago has to offer.

Don’t fall asleep!
There are still 5 more things to do in Chicago!

11- Wabash Art Street

Surely you’ve seen the famous deer mural on Instagram, right? Well, it’s on Wabash Art Street, a street full of murals right in downtown.

Honestly, it was a bit disappointing. There are some nice murals, but they’re quite spread out, and it’s not really a lively neighborhood to spend much time in. If you enjoy street art, it can be an interesting stroll, but in my opinion, it’s not a must-see in Chicago.

12- Explore The Loop

The Loop is Chicago’s financial and tourist heart. Everything is within reach here: clean streets, top shops, impressive skyscrapers, and that big-city vibe that never sleeps (although, as I mentioned before, it quiets down quite a bit at night).

A nice architectural detail is the elevated bridge that crosses part of the neighborhood, giving its streets a unique character. Additionally, at the edges of the Loop, you’ll find two iconic stops:

1- Sign marking the beginning of Route 66

2- Classic café where many travelers start with their first breakfast before embarking on this legendary adventure.

13- Jazz Club

Chicago is synonymous with jazz and blues. The Windy City became a global capital for these genres after Black communities popularized them, and today it remains one of its great cultural prides.

Almost every night you can find bars and restaurants with live music, some very historic, like the Green Mill Cocktail Lounge (legendary, open since 1907) or Buddy Guy’s Legends, where Buddy Guy himself often performs.

The experience usually costs around 50 USD per person, with most venues charging an entrance fee or requiring a minimum consumption. My tip: head a little outside the Loop to find more local and authentic spots, and experience jazz the way it’s truly lived in Chicago. No need to book tours! 

14- Skydeck, Willis Tower

In the iconic Willis Tower (formerly Sears Tower) stands Chicago’s most famous observation deck: the Skydeck. Its main attraction is the glass box on the 103rd floor, where you can literally feel like you’re floating above the city.

Before reaching the observation deck, the route offers several photo spots showcasing iconic moments and symbols of Chicago: from a deep-dish pizza to the tower’s antennas, a CTA train passing through the neighborhoods, or the classic Route 66 sign. Everything is designed to make the wait an entertaining experience.

That said, to enter the famous glass boxes, you have to join a separate (and quite long) line. One detail that disappointed me: each person is only allowed 1 minute (or 2 if you go with someone). A timer sounds when your time is up, which makes the experience feel a bit rushed. Also, while walking on glass and seeing the buildings far below is mind-blowing, the best panoramic views are actually on the opposite side of the observation deck, not from the box.

Ticket prices vary depending on the time of day: $28 in the morning, $30 during the day, and $35 from sunset onwards.

15- Chicago Theater

Probably the most famous sign in Chicago is the illuminated “Chicago” sign, located above State Street and part of the historic Chicago Theater.

Opened in 1920, it features a main auditorium with over 3,600 seats and an interior that combines French details with classical architecture, leaving visitors impressed.

You can take a guided tour to discover its secrets inside or, even better, attend a live concert or show and experience it in action.

YAPA - Architectural Riverwalk Tour

If there’s one activity that defines Chicago, it’s its architectural riverboat tour. Over 90 minutes, you’ll cruise past the city’s most iconic buildings while a guide explains the history and architectural significance of each one. If this type of tour isn’t your thing but you still want to see the skyscrapers from the river, here’s an alternative sunset cruise option.

Tips for Traveling to Chicago on a Budget

The United States is generally expensive, but that doesn’t mean you can’t travel “cheap.” There are always little tricks to save… and if there are, I’ll find them 😏. Here are some backpacker tips:

• Cheap flights: Use Skyscanner as a meta-search engine. It lets you see entire months, nearby airports, and the cheapest combinations.
• Budget accommodation: For hostels, nothing beats Hostelworld. I booked HI Chicago, right in the Loop, for 35 USD per night. If you’re traveling as a pair, you can even get a private room for that price per person.
• Cheap eats (and a fun twist): the Too Good To Go app is growing in cities like New York and Chicago. It offers “surprise bags” with leftover food from local businesses at a much lower price. Perfect for grabbing something the night before and having breakfast the next day. We’re talking sandwiches or croissants for just 3 USD in Chicago!
• Plan ahead: organize your itinerary by neighborhoods and walk as much as possible. This way, you save on transportation, which in the United States can be quite expensive.

With these tips, you can enjoy Chicago without breaking the budget. In the end, the most important thing is to try a deep dish pizza and get lost among the skyscrapers of the Windy City.

-> If you want to see more, in my Instagram highlights (@guadiviajando) I’ve shared a minute-by-minute recap of this trip (and many more). And if Chicago is just a small part of your trip to the United States, you can check out this page with lots of information about other destinations in the country.

That’s a wrap, travelers! I hope you have an amazing time in Chicago and get spectacular weather. Any questions? Feel free to reach out on my Instagram.

Kisses and good vibes! 💛

Guadi.