Three-day Romantic Getaway to Chicago.

Experience the Windy City's romance and charm with your loved one in Chicago.

22 April 2023

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.

Travel plan

Getting latest place information
Day 1

Chicago Magic

  • Check into The Langham, a luxurious, romantic hotel in the heart of downtown Chicago
  • Start off the day with a visit to the Art Institute of Chicago, home to thousands of artworks from around the world
  • Grab lunch at Eataly, a massive Italian marketplace with a variety of food options
  • Take a stroll along the Chicago Riverwalk, stopping to admire the city's stunning architecture
  • End the evening with a magic show at the famous Chicago Magic Lounge, complete with cocktails and a vintage ambiance
Day 2

Windy City Wonders

  • Start the day with brunch at Yolk, a popular breakfast spot known for their creative dishes
  • Explore Navy Pier, a popular attraction with rides, restaurants, and stunning views of Lake Michigan
  • Walk through Millennium Park, home to the iconic "Bean" sculpture and a variety of outdoor art pieces
  • Grab a Chicago-style deep dish pizza for dinner at Lou Malnati's or Giordano's
  • Finish off the night with a show at the famous Second City comedy club, known for launching the careers of comedy legends
Day 3

Chicago Culture

  • Start the day with a guided architecture tour of Chicago's famous skyscrapers
  • Visit the Field Museum, home to extensive natural history exhibits including Sue, the largest complete T.rex skeleton
  • Grab lunch at Portillo's, a classic Chicago hot dog and Italian beef spot
  • Explore the vibrant neighborhoods of Wicker Park and Bucktown, known for their arts and culture scene
  • End the trip with a visit to the Lincoln Park Zoo, a free zoo with a variety of animals and beautiful park grounds.

How to get there

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.

More travel plans

Chicago in Four Days: A Budget Adventure.

Chicago is a vibrant and culturally-rich city located on the shores of Lake Michigan. For a budget-friendly trip, be sure to take advantage of free attractions such as the Lincoln Park Zoo and Millennium Park. Chicago is also known for its world-class cuisine, so be sure to sample the iconic deep-dish pizza and other cheap eats.

5-Day Romantic Getaway in Chicago, USA

A romantic trip to Chicago, United States is the perfect opportunity to explore the Windy City together. You can take a stroll along the picturesque Lake Michigan shoreline, indulge in mouth-watering cuisine at award-winning restaurants, and take in the breathtaking views from the Willis Tower. With a wide range of cultural and entertainment options, Chicago provides the ideal backdrop for a memorable romantic getaway.

Windy City Wonders: A 4-Day Family Adventure in Chicago!

Experience the vibrant city of Chicago on a family friendly trip filled with unforgettable memories. Explore the iconic Millennium Park, where kids can splash in the Crown Fountain or marvel at the reflective Bean sculpture. Indulge in delicious deep-dish pizza, visit the Shedd Aquarium or catch a baseball game at Wrigley Field for an action-packed getaway in the Windy City.

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.