Two-Day Windy City Romance Guide

Fall in love all over again in the Windy City.

03 May 2023

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.

Travel plan

Getting latest place information
Day 1

Windy City Romance

  • Check into the luxurious Waldorf Astoria Chicago, complete with marble bathrooms and a Michelin-starred restaurant.
  • Take a stroll hand in hand along the iconic Navy Pier, enjoying the stunning views of Lake Michigan.
  • Hop on a romantic cruise down the Chicago River, learning about the city's history and architecture from a knowledgeable guide.
  • Indulge in a delightful dinner at Alinea, a three-Michelin-starred restaurant dishing up avant-garde cuisine that will tantalize your taste buds.
  • Finish off the evening with a nightcap at the grown-up playground, Punch Bowl Social, for some cocktails and playful games.
Day 2

Discovering Chi-Town's Charm

  • Fuel up with breakfast at the chic and cozy Milk Room, where you can sip on rare vintage spirits paired with delectable bites.
  • Take a leisurely walk through the charming Lincoln Park Zoo, where you can spot everything from gorillas to sea lions.
  • Get some cultural fix at the Art Institute of Chicago, home to an impressive collection of artworks from around the world.
  • Delight in an authentic deep-dish pizza at the famous Lou Malnati's Pizzeria, where the buttery crust and gooey cheese will satisfy your tastebuds.
  • Sip on some cocktails at the speakeasy-inspired The Violet Hour, complete with dim lighting and live jazz music.
  • Your two-day escapade in Chicago promises to be a memorable one full of romance, culture, and delicious cuisine.

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

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.

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.

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.

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.