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

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 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.

Chicago on a Budget: The 5-Day Adventure

Exploring Chicago on a limited budget is possible with the city's many free attractions including Millennium Park, Navy Pier, and the Lincoln Park Zoo. Budget-friendly accommodations can be found in the city's hostels and Airbnb's located in the trendy neighborhoods of Wicker Park and Logan Square. Delicious local cuisine at affordable prices can also be found in the city's diverse dining scene ranging from deep-dish pizza to ethnic street food.

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.