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.

How long are you staying?

Romantic stays

Stays on a budget

Family-friendly stays

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

Romantic Long Weekend in Philadelphia

Philadelphia, a city rich in history and culture, offers the perfect romantic getaway for couples. Explore historic landmarks like Independence Hall and the Liberty Bell, stroll through picturesque parks like Rittenhouse Square, and indulge in decadent food and drink at one of the city's many renowned restaurants and bars. End your days in luxury at a cozy bed and breakfast or boutique hotel.

Adventure-packed Day Trip to San Diego, USA!

San Diego offers a perfect family-friendly getaway with its beautiful beaches, vibrant culture, and abundance of attractions for all ages. Explore the famous San Diego Zoo, indulge in thrilling rides at Legoland, or soak up the sun at Coronado Beach. With endless outdoor activities, delicious dining options, and a laid-back atmosphere, San Diego is the ideal destination for an unforgettable family vacation.

Romantic Weekend Getaway: Austin, United States

Experience the vibrant and eclectic atmosphere of Austin with your significant other. Stroll hand-in-hand through the picturesque Lady Bird Lake and enjoy a picnic with a stunning view of the Austin skyline. Indulge in the city's famous live music scene while sipping on craft beers and enjoying delicious Texas cuisine.

San Francisco's Best Day Trip Adventure!

Explore San Francisco's major landmarks and attractions such as the Golden Gate Bridge, Alcatraz Island, and Fisherman's Wharf. Hike up to Twin Peaks for a breathtaking view of the city skyline and browse the local shops and eateries in the vibrant neighborhoods of Chinatown and Haight-Ashbury. Save money by taking advantage of public transportation options like the iconic cable cars and buses.