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.

Save destination

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!

How long are you staying?

1 days

Chicago Adventure: Cultural Foodie Fun

A trip to Chicago, known as the "Windy City," is a perfect choice for culture-seekers and foodies alike. Filled with architectural gems, world-renowned museums, and diverse neighborhoods, there's no shortage of things to explore. Don't leave without trying Chicago-style deep-dish pizza and taking a stroll along the picturesque Lake Michigan shoreline.

2 days

2-day Chicago Adventure: Art, Food, and Culture!

A trip to Chicago as a tourist would include exploring famous landmarks such as the Willis Tower and Navy Pier. One would enjoy visiting cultural attractions like the Art Institute of Chicago and the Museum of Science and Industry. Lastly, experiencing the city’s unique food scene, including deep-dish pizza and Chicago-style hot dogs, would be a must.

3 days

The Ultimate 3-Day Chicago Adventure

Chicago boasts an impressive skyline and rich cultural diversity that attracts visitors from all over the world. Iconic landmarks such as the Willis Tower and Millennium Park provide excellent photo opportunities, while a stroll along the Magnificent Mile offers an extensive array of shopping, dining, and entertainment options. For a taste of Chicago's famous cuisine, deep-dish pizza and Chicago-style hot dogs are a must-try.

4 days

4-Day Fun-Filled Guide to Chicago, USA

Chicago is a vibrant city full of diverse neighborhoods, impressive architecture, and a world-renowned food scene. Visitors can take in breathtaking views of the skyline from the Willis Tower Skydeck, stroll along the Lakefront Trail, and explore world-class museums and galleries. With something for everyone, a trip to Chicago is not to be missed.

5 days

5-Day Adventure Guide to Chicago, USA

Chicago is a bustling metropolis on the shores of Lake Michigan, known for its architecture, food, and culture. Tourists can explore the city's many museums and parks, including the Art Institute of Chicago and Millennium Park. Be sure to sample the city's famous deep-dish pizza and catch a game at Wrigley Field or Soldier Field.

Romantic stays

Chicago in a Day: Romance and Adventure

A romantic trip to Chicago, United States offers a perfect blend of scenic beauty and metropolitan charm. Take a romantic stroll by the lakefront or catch breathtaking views from the Willis Tower. Experience culinary delights at the famous eateries, and don't miss out on the city's vibrant arts and culture scene.

Two-Day Windy City Romance Guide

Chicago offers a perfect backdrop for a romantic trip with its picturesque skyline and waterfront views. The city’s rich history, lively culture, and delicious food make it an ideal destination for couples who want to experience the ultimate romantic getaway. Take a stroll on the stunning Lakefront Trail, grab some deep-dish pizza, and catch a show at one of its renowned theaters for an unforgettable romantic trip.

Three-day Romantic Getaway to Chicago.

Embark on a romantic getaway to Chicago, the Windy City and explore its stunning architecture, exciting nightlife and culinary scene. Take a stroll hand-in-hand down the Magnificent Mile, enjoy a sunset gondola ride on the Chicago River, and top off your evening with a romantic candlelit dinner at one of the city's top-rated restaurants. With its charm and elegance, Chicago is sure to ignite the romance in any couple.

Stays on a budget

Chicago on a Budget: A Day of Adventure

Visiting Chicago on a limited budget is still possible with some careful planning. Opt for budget-friendly accommodation options such as hostels or Airbnbs in less touristy neighborhoods. Take advantage of public transportation and free activities such as visiting Millennium Park, the Lincoln Park Zoo, and exploring the city's diverse neighborhoods for a fun and affordable trip to Chicago.

Discovering Chicago's Windy Wonders on a Budget

Visiting Chicago on a limited budget is possible and rewarding. Explore iconic attractions like Millennium Park and the Magnificent Mile, while also taking advantage of free events hosted throughout the city. Save money on accommodations by booking a hostel or budget-friendly hotel, and take advantage of the city's excellent public transportation system to get around easily.

Chicago on a Budget: 3-Day Adventure Guide

Chicago is a vibrant and exciting city that can be enjoyed on a limited budget. Visitors can take in panoramic views from the top of Willis Tower, explore the diverse neighborhoods of Lakeview and Wicker Park, and visit the free-admission museums such as the Art Institute of Chicago. To save on accommodation costs, travelers can opt for budget-friendly hostels or seek out affordable Airbnb rentals.

Family-friendly stays

Chicago Fun Frenzy: Explore, Indulge, and Immerse!

A trip to Chicago offers a plethora of family-friendly activities and attractions. Explore the iconic Navy Pier where you can enjoy rides, games, and spectacular views of Lake Michigan. Immerse yourselves in the vibrant culture of the city by visiting Millennium Park, home to famous landmarks like "The Bean" and a host of interactive public art installations. Finally, don't forget to indulge in Chicago's deep-dish pizza and explore the numerous museums and zoos that cater to children's interests.

Discover Chicago: A Family-Friendly Adventure on a Budget

A family-friendly trip to Chicago offers a perfect blend of fun and educational activities. Explore the interactive exhibits at the renowned Field Museum, embark on a scenic boat tour along the Chicago River, and get a stunning, panoramic view of the city from the Skydeck Chicago. Don't forget to indulge in some deep-dish pizza and visit the beloved Lincoln Park Zoo during your visit!

Chicago on a Budget: Three Days of Fun!

A family friendly trip to Chicago, United States offers an exciting blend of entertainment and education for all ages. Explore the iconic Navy Pier with thrilling rides, beautiful gardens, and stunning lake views. Immerse yourself in the city's rich history by visiting unique museums like the Shedd Aquarium, Field Museum, and the interactive Chicago Children's Museum.

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.

Romantic Long Weekend: San Diego Hidden Gems

San Diego is a charming destination that offers couples scenic beauty, delicious cuisine, and excellent-to-good beaches. From exploring the trendy Gaslamp Quarter to strolling through romantic La Jolla, there's no shortage of activities for lovebirds. Besides, a sunset sail on the harbor followed by an intimate dinner overlooking the ocean is the perfect way to end a romantic day in San Diego.

4 Days of Fun in Austin, Texas

Austin, the capital of Texas, is a vibrant city known for its live music scenes, outdoor activities, and delicious food. Visitors can explore the trendy South Congress Avenue, take a dip in the natural springs, and indulge in some authentic Tex-Mex cuisine. A must-see attraction is the State Capitol building, which gives insight into the history and culture of Texas.

San Francisco in 5 Days: Budget and Fun

A trip to San Francisco on a limited budget can be an exciting adventure with plenty of inexpensive attractions to explore. From the iconic Golden Gate Bridge and Fisherman's Wharf to the lively Haight-Ashbury neighborhood and the free-entry Golden Gate Park, there is no shortage of sights to see. Accommodation options range from budget hostels to affordable motels, and cheap dining alternatives include street food, food trucks, and farmer's markets.