Chicago Travel Plans

Welcome to the Windy City, where the people are friendly, the pizza is deep, and the weather is unpredictable enough to keep things interesting. Just make sure to hold onto your hats (and your deep dish) while you're here.

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Best of lists

15 perfect restaurants in Chicago, United States

Welcome to the windy city of Chicago, where deep-dish pizzas reign supreme and culinary delights await at every corner. A recent gastronomical expedition has unearthed the city's 15 best restaurants, bursting with flavors that will make your taste buds tap-dance with joy. From charming Italian trattorias that will have your grandmother nodding in approval to avant-garde eateries that redefine the term "food experience," Chicago has got your cravings covered. Just remember to bring an empty stomach and a stretchy waistband – trust us, you'll need them both!

Best 20 things to do in Chicago, United States

Welcome to the Windy City, where our list of the best 20 things to do in Chicago is as varied and colorful as the city itself. Start your adventure with a sunset stroll along the picturesque Riverwalk, because nothing says romance like avoiding cyclists whizzing past you. Feeling peckish? Head to the veritable heaven of deep-dish pizza joints and indulge in a cheesy, saucy delight that solves any existential crisis. Finally, no trip to Chicago would be complete without immersing yourself in our world-renowned blues scene, where you can dance the night away and pretend you have rhythm. Enjoy your time in the vibrant city that effortlessly merges Midwestern charm with big-city attitude!

The very best 12 nightlife spots in Chicago, United States

Welcome to the Windy City, where the nightlife is as vibrant as the Bulls during their prime! Start your nocturnal adventures at "The Drunken Goat," a mysterious tavern tucked away in a hidden alley - rumor has it, it's a favorite haunt of famous jazz-loving goats. For an out-of-this-world experience, visit "Galactic Lounge," where the space-themed décor will have you feeling like a cosmonaut on a disco moonwalk. Finally, unleash your inner party animal at "The Roaring Lion," a speakeasy that transports you back to the roaring 20s, complete with flapper dancers and bootlegged cocktails that would make Gatsby himself tip his hat.

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Family-friendly stays

How to get to Chicago


The best way to get to Chicago by plane is to fly into O'Hare International Airport or Midway International Airport, both of which are served by major airlines from most major cities in the world. You can check prices and schedules on websites like Expedia or Kayak.


The best way to get to Chicago by car is to take one of the major highways, such as I-90 or I-94, which both run through the city. However, be aware of traffic congestion during peak travel times.


The best way to get to Chicago by train is to take an Amtrak train, which connects the city to other major cities in the United States, such as New York, Washington D.C., and Los Angeles. The main train station in Chicago is Union Station.


The best way to get to Chicago by boat is to take a ferry from Navy Pier to locations such as Michigan City or St. Joseph. However, this mode of transportation is not as common as the others and may have limited availability depending on the season.


The best way to get to Chicago by bus is to take a Greyhound bus, which connects the city to most major cities in the United States. The main bus station in Chicago is the Greyhound Station.

Explore elsewhere

Philly Fun Fest: 5 Days of Budget-Friendly Family Adventures

A family friendly trip to Philadelphia offers a perfect blend of history, culture, and entertainment for all ages. Start by exploring the iconic historical sites like Independence Hall and the Liberty Bell, immersing yourself in America's rich heritage. Enjoy family-oriented attractions like the Please Touch Museum or the Adventure Aquarium, before indulging in delicious local cuisine such as Philly cheesesteaks or soft pretzels.

San Diego: Family Fun on a Budget

A family-friendly trip to San Diego offers a diverse range of activities and attractions for all ages. Your family can explore world-class zoos, such as the San Diego Zoo and the Safari Park, to get up close and personal with exotic wildlife. Enjoy the sunny beaches, visit the USS Midway Museum, and take a stroll along the vibrant and historic Gaslamp Quarter for a memorable vacation in the beautiful city of San Diego.

Austin's Adventurous Family Excursion: 4 Days of Fun

Embark on a delightful family-friendly trip to Austin, Texas, where a vibrant blend of culture, outdoor activities, and delectable cuisine awaits. Explore the city's iconic landmarks, from the towering State Capitol to the beloved Barton Springs Pool, perfect for swimming and picnicking. Discover interactive museums like the Thinkery, and end the day with a mouth-watering barbecue feast at one of the city's legendary smokehouses.

San Francisco: A Fun-Filled 3-Day Adventure!

A family-friendly trip to San Francisco offers a plethora of attractions and activities to keep everyone entertained. Explore the iconic Golden Gate Bridge and indulge in picturesque views from Twin Peaks. Take a delightful cable car ride, visit the interactive Exploratorium, and enjoy a fun-filled day at the California Academy of Sciences, making it a memorable vacation for all.