Chicago Travel Guides

Super useful & totally free Chicago travel guides, written by locals who love Colorado

Why We Love Chicago: Chicago is known for a lot of things: the Bean, deep-dish pizza, sports, and so much more. These things are all iconic to the city, but the Windy City doesn’t stop there. For being one of the biggest cities in America, Chicago doesn’t feel overwhelming. The people are welcoming, there are tons of unique neighborhoods to explore, and visitors and locals alike will find that there’s always something to do. Not to mention, with Lake Michigan nearby and incredible architecture all around, there’s something to admire at every turn.


Best of Chicago

Things to Do

View of people and the Bean in Millennium Park
The Bean in Millennium Park on a clear day

Chicago has no shortage of things to do. Explore the city and local neighborhoods, and take in historic sites. These are my top recommendations:

  • Millennium Park – This is where you’ll find the Bean! It’s close to other attractions and a great spot for some city views.
  • The Art Institute – Chicago’s premier art museum with an impressive collection worth seeing.
  • Walk along the Chicago River – A central place to explore, sightsee, and take some great pictures. 
  • Explore the food scene – Chicago has just about every cuisine you can imagine. Try something new and enjoy a tasty meal. 
  • Head to Lake Michigan – A refreshing change of scenery with beautiful views of the lake and city skyline.

👉 Explore all things to do in Chicago.


🗺️ Where to Stay

Depending on why you’re visiting Chicago, the neighborhood you choose to stay in may vary. But generally, these are the best and most central neighborhoods:

  • The Loop – The center of downtown Chicago. Close proximity to museums, attractions, restaurants, and shopping.
  • River North – Close to the Magnificent Mile and Riverwalk on the Chicago River. Upscale area with fine dining and nightlife.
  • West Loop – A great place for foodies to stay. Upscale restaurants, casual eats, and local joints all around.  

👉 Read the complete guide to where to stay in Chicago.

The author looking at the Chicago River
Travel Lemming writer, Lea Rose, at the Chicago River between the Loop and River North

🛎️ Best Hotels

The Drake hotel building in Chicago from the outside
(photo: Leonard Zhukovsky / Shutterstock)

Chicago is filled with hotels to suit everyone’s needs and preferences. Below are my picks for three different options, depending on what you’re looking for:

  • The Drake – A historic, luxury hotel at the corner of Lake Michigan and the Magnificent Mile.
  • Hyatt Place Chicago/Downtown-The Loop – A classic, clean, and modern hotel with amenities located in the heart of the Loop.
  • The Publishing House Bed and Breakfast – A beautifully designed boutique hotel with great hospitality, located in the West Loop.

🍽️ Restaurants

Chicago is known for its incredible food scene. No matter your taste buds or budget, you’ll be able to find something delicious:

  • Lou Malnati’s – Stop here for your classic Chicago deep dish pizza.
  • Etta – Fresh and seasonal comfort foods like wood-fired pizza and pasta. A nice restaurant with a warm atmosphere.
  • Kasama – A modern Filipino restaurant and bakery serving up delicious breakfast and lunch options. 
  • Time Out Market – Trendy food hall with restaurant vendors from all over Chicago. A lot of food options and good for groups.
  • Beatnik on the River – Mediterranean restaurant with beautiful decor and a bright atmosphere. Located right along the river.

👉 Read the full list of 33 best restaurants in Chicago.

The entrance to Etta in Bucktown and a wall art of chicken
Etta – Bucktown location

🚗 Day Trips

Overlooking view of buildings in Downtown Milwaukee
Views of downtown, Milwaukee
  • Milwaukee, WI – A smaller city with a great downtown area, river and lake access, and hopping beer scene.
  • Holland, MI – A charming small town with a Dutch twist. See canals, windmills, tulips, and more. Fun for the whole family. 
  • Michigan City, IN – A small lakeside city that’s close to Indiana Dunes National Park and other small towns. 
  • Oak Park, IL – Enjoy arts and culture, and a visit to the Frank Lloyd Wright Home & Studio. 
  • Lake Geneva, IL – A resort town with a rich architectural history, friendly downtown, and tons of outdoor activities.

👉 Read the complete guide on day trips from Chicago.


🏘️ Neighborhoods

Cars and establishments in Downtown Wicker Park
“Downtown” Wicker Park
  • Lincoln Park – Charming downtown spots to explore, great shopping and dining, and close to the park and zoo. 
  • River North – Trendy and modern area with lots of museums, galleries, restaurants, and options for nightlife. 
  • West Loop – An upscale, yet industrial vibe. West Loop is home to Fulton Market district, which has amazing dining options.
  • Wicker Park – An artsy neighborhood with lots of cool, local shops and restaurants. 
  • Gold Coast – An architectural gem with historic homes and buildings, only a short walk to Lake Michigan.

👉 Read the full list of 18 best Chicago neighborhoods.

🍸 Bars

A man holding a glass of whiskey and bottles of whiskey on the table
Enjoy a drink at one of Chicago’s many bars
  • Howl at the Moon – Energetic bar in River North that’s great for live music, singing, and dancing.
  • Nights and Weekends – Funky and trendy bar in the West Loop. Cool vibes, good music and DJ, and a dance floor in the back.
  • Cindy’s Rooftop – Stylish rooftop bar in the heart of the Loop. Great ambiance, specialty cocktails, and beautiful city views.
  • Fadó – (Pronounced F’doe) An Irish pub great for sports fans and beer lovers. Located in River North.
  • Roscoe’s Tavern – LGBTQ bar in Lake View. Fun and lively atmosphere with drink specials, events, and an outdoor patio.

🏛️ Best Chicago Museums

A lion statue on the entrance of The Art Institute
Entrance to the Art Institute
  • The Art Institute – A huge museum to wander and witness artwork from around the world, and throughout history.
  • Contemporary Museum of Art – A museum of contemporary artwork that features rotating exhibits.
  • Museum Campus – A 57-acre park that includes the Field Museum, Shedd Aquarium, and Adler Planetarium.
  • Chicago History Museum – Learn all about Chicago’s story and history with permanent and rotating exhibits. 
  • Chicago Children’s Museum – Located on Navy Pier, this is an educational and immersive museum meant just for kids.

👉 Read the full list of 20 best museums in Chicago.

🆓 Best Free Activities

View of meerkats at the Lincoln Park Zoo in Chicago
Visit some Meerkats at the Lincoln Park Zoo
  • Lincoln Park Zoo – This 35-acre zoo has a variety of wildlife exhibits and some interactive wildlife experiences.
  • Chicago Cultural Center – A cultural and historical hub known for its free arts events and two stained-glass domes.
  • Garfield Park Conservatory – The largest conservatory in America with extensive outdoor landscapes and greenhouses.
  • Lincoln Park Conservatory – A vibrant greenhouse and botanical garden located within the city in Lincoln Park.
  • Harold Washington Library Center – Chicago’s public library has over a million books, beautiful architecture, and a winter garden.

🌳 Best Outdoor Attractions

View of the coastline of Chicago from Lakefront Trail
The Lakefront Trail offers sweeping views of Chicago’s coastline
  • Riverwalk – A 1.25-mile walking trail through the center of the city and along the Chicago River.
  • Lakefront Trail – 18 miles of coastline with incredible city and lake views. Perfect for walking, running, and biking.
  • The “606” – An elevated, urban greenspace that goes for 2.7 miles and connects different neighborhoods.
  • Lincoln Park – Over 1,000 acres of park that runs along the lakefront, including several of the best Chicago beaches.
  • Grant Park – 300 acres of green space, and arts and culture attractions in the downtown Loop.

🏙️ Best Attractions for Architecture

View of an Architecture Cruise on the Chicago River
An architecture cruise takes visitors by some of Chicago’s most iconic buildings
  • Architecture Cruise – A great way to sightsee and learn about Chicago’s architecture while seeing the buildings up close. 
  • theMART – Also known as the Merchandise Mart, this historical landmark was once the biggest building in the world. 
  • Frank Lloyd Wright Home & Studio – Located in Oak Park, this is the home and studio of American architect, Frank Lloyd Wright.
  • Rookery Building – A late 19th-century skyscraper with iconic features, architectural details, and rich history.
  • Robie House – A distinctly American, prairie-style home designed by Frank Lloyd Wright, located in Hyde Park. 

Chicago Travel Advice

🗓️ Best Time to Visit

Chicago has very cold winters, but also really hot summers. In spring and fall, the weather can flip flop from hot to cold. 

  • 🌞 Summer – My favorite season in Chicago. Days are hot, but the city is active and the lake is refreshing.
  • 🍂 Fall – Cool, pleasant weather for walking and exploring. Lots of parks to see fall foliage. 
  • 🌼 Spring – Cool, but sunnier days where you’ll still need a jacket or coat.
  • ❄️ Winter – The weather is cold and it snows often. Dressing in layers is essential.

🚌 Getting Around

Chicago is fairly easy to navigate. Public transportation is convenient, and you can cover a lot of ground just by walking. 

  • 🚶‍♀️ Walking – Chicago is a very walkable city as long as you plan on staying within a few neighborhoods. 
  • 🚗 Driving – Overall, Chicago is very driveable although parking can be difficult and pricey. See our full guide to driving in Chicago for tips
  • 🚇 Public Transit – This is the best way to get around. The CTA operates trains (The “L”) and buses throughout the city.
  • 📲 Ride Share – Ubers and Lyfts are almost always available. Know that ride share prices can vary based on time and location.
  • 🚴‍♀️ Biking – Chicago is bike-friendly. There are bike lanes and Divvy rentals throughout the city, too. 
  • 🛴 Scooters – Electric scooters are available in Chicago, but not allowed on the 606 and Lakefront trails.

👉 Read our full guide to getting around Chicago.


👉 Tips & Things to Know

  • 🪪 – ID & Vaccination Card – Depending on Covid mandates, many indoor places will require you to present an ID and vaccine card for entry.
  • 🚈 – Ventra Card – You’ll need a Ventra card to ride public transportation. You can buy one online, at any train stop, or at various shops. 
  • 🍽️ – Reservations – In order to avoid long wait times or running around, always try and make reservations, if possible.
  • 💬 – Midwestern Hospitality – Don’t be afraid to say hello to people–Chicagoans are friendly.
  • 🏡 – Neighborhoods – Chicago is full of charming and unique neighborhoods. Be sure to spend some time exploring them.

🧳 What to Pack

  • 🧥 – Layers – Weather can be unpredictable with the Lake effect. To be safe, dress in layers.
  • 👟 – Good Walking Shoes – You’re likely to be on your feet all day, so having comfortable walking shoes is a must.
  • 🥾- Waterproof boots – If you plan on visiting in the winter, pack boots or shoes that are waterproof with good grip. 
  • 🛍️ – Reusable Bags – A lot of places in Chicago charge a fee for plastic bags, so bring your own reusable ones instead.
  • 👜 – Belt Bags – Lots of people in Chicago use belt bags as purses. It’s a good way to keep your items accessible and close to you.
  • 🕶️ – Sunglasses – Shield your eyes from the sun, wind, and even bright snow.

🤓 Facts & Info

  • Census Population (2020) – 2,671,635 (city), 9,618,502 (metro area)
  • Time Zone – Central Standard Time (UTC -6 / UTC -5 during daylight savings)
  • Area Codes – 312, 773, and 708
  • Airports – O’Hare International Airport (ORD), and Chicago Midway International Airport (MDW)
  • Nickname – the Windy City, Chi-Town, the Second City
  • Demonynm – Chicagoan
  • State – Illinois
  • CountryUnited States of America

💵 Costs & Budgeting

  • 3 Star Hotel Room – $120-$200/night
  • 1 Bedroom Apartment Rental – $100-$200/night
  • Rental Car – $100-$200/day
  • Public Transit Ticket – $5 day pass ($2.50 to airport from center)
  • Ride Share from Downtown to Airport – $40
  • Take Out Meal for Two – $40-$60
  • Sit Down Dinner for Two – $50-$75
  • Draft Beer – $7-$10

FAQs About Visiting Chicago

Is Chicago safe for tourists?

Chicago is safe for tourists, however, like most big cities, Chicago has its fair share of crime. Being aware of your surroundings can go a long way. Keep personal items like purses and bags close to you, and exercise extra caution at night time. As far as neighborhoods go, as long as you stick to the downtown, populated areas, you should be fine.

When is the best time to visit Chicago?

Spring and fall are the most recommended times to visit Chicago. The weather is mild and great for exploring the city on foot. However, locals will tell you that summers in Chicago are unmatched. If you do plan on visiting in the summer, though, know that the city can get really crowded and hot.

How many days should I spend in Chicago?

3-5 days is the amount of time recommended for visitors. This should give you enough time to see the sights and visit major attractions. Chicago is a big city with a lot to offer, so how tightly you pack your itinerary depends on what you’re looking to do. For a more leisurely trip with some time to explore, five days should be enough.

Where should I stay in Chicago?

The Loop, or close to it, is where most visitors tend to stay. That being said, there are a lot of advantages to staying in other neighborhoods–prices may be lower, accommodations will be more low-key, and your experience is likely to be less “touristy.” The North side and Lincoln Park are good options.

Which airport should I fly into?

Chicago has two airports: O’Hare and Midway. Both are international airports and have train access into the city. Which airport you decide to fly into will depend on a few factors. O’Hare has a wider range of airlines that fly in and out of the airport, so you’re likely to have more flight options here. Midway is technically closer to the city distance-wise, but the airlines are limited.


Meet Our Chicago Travel Experts

Lea Rose Allbaugh

Lea Rose Allbaugh is a Chicago-based freelance writer who’s obsessed with all things travel. She caught the travel bug back in 2015 during an exchange to the Netherlands and has traveled to 13 other countries since. Travel writing is her favorite way of inspiring others to get up and go experience the world. In her free time, she loves to eat pasta and make everything a dance party. She also writes at her website, Written World!

👉 Read Lea Rose’s Articles

Nilani Thiyagarajah

Nilani Thiyagarajah is a freelance writer and editor in Chicago, Illinois. Nilani enjoys exploring the Windy City whenever she has free time. Having grown up in Cincinnati, Ohio, she enjoys seeking and finding all of the best-kept secrets that any area has to offer. Nilani loves traveling and learning about new cultures and plans to do a lot more of it in the coming years!

👉 Read Nilani’s Articles


📰 Illinois Travel Guides

Chicago is the third-largest city in America, and as someone who moved here after one visit, it’s easy to see why it’s such a popular destination. There are a ton of things to do in Chicago, and the region has a lot to offer in terms of cities and natural beauty.


🗺️ Chicago Map