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!

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.

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!

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How to get to Chicago

Plane

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.

Car

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.

Train

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.

Boat

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.

Bus

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's Cultural Delights: A 2-Day Getaway

A romantic trip to Philadelphia, United States promises to be filled with historic and cultural delights. Take a stroll hand-in-hand through the charming streets of Old City before enjoying a candlelit dinner at the stylish Rittenhouse Square. Don't miss the iconic Philly cheesesteak and end the night with a kiss atop the steps of the Philadelphia Museum of Art.

A Romantic Long Weekend in San Diego

A romantic trip to San Diego, United States promises a delightful blend of coastal charm and urban energy. With golden beaches, iconic attractions like Balboa Park and the Gaslamp Quarter, and a plethora of restaurants, cafes, and bars, you'll have plenty of opportunities for strolling hand in hand, enjoying candlelit dinners, and soaking up the laid-back vibe of California. From whale-watching tours to sunset sails, there are also plenty of activities to add some adventure and excitement to your trip.

Discover Hipster Austin in a Long Weekend

A romantic trip to Austin, United States offers a perfect blend of natural beauty, rich history, and contemporary urban vibes. You can stroll hand in hand through the beautiful Zilker Park or soak in the stunning sunset at Mount Bonnell. Add some spice to your trip by exploring the local music scene and savoring some delicious Tex-Mex cuisine.

A Romantic Long Weekend in San Francisco

A trip to San Francisco for a romantic getaway promises breathtaking views, delightful experiences, and unparalleled excitement. The city offers a range of things to do, from exploring the Golden Gate Bridge to indulging in fine cuisine or enjoying a romantic sunset at Baker Beach. With its charming ambiance, iconic attractions, and vibrant culture, San Francisco is the perfect destination for couples looking to create beautiful moments together.