Three-day Romantic Getaway to Chicago.
Experience the Windy City's romance and charm with your loved one in Chicago.
22 April 2023
Sophie Watts
US Travel Writer
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

- 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
- 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
- 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.
Length of stay
Type of trip
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.