
Chicago Romantic Vacations
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Discover romance in the Windy City's captivating ambiance
Chicago is renowned for its urban charm, towering skyscrapers, world-class theater productions, stunning architecture, and impressive museums that showcase art and history. The city is dotted with iconic monuments and offers a vibrant entertainment scene that caters to all tastes. Beyond the city limits, visitors can explore the breathtaking natural scenery, indulge in shopping sprees at upscale boutiques, or uncover hidden gems in charming neighborhoods. With its diverse attractions and captivating ambiance, Chicago promises an unforgettable romantic getaway filled with endless possibilities.
Top Romantic vacation packages in Chicago

Hotel Felix River North/Magnificent Mile
Reviewed on Apr 24, 2025

The Royal Sonesta Chicago River North
Reviewed on Apr 24, 2025


Trump International Hotel & Tower Chicago
Reviewed on Apr 22, 2025

Radisson Blu Aqua Hotel Chicago
Reviewed on Apr 21, 2025
5* Romantic vacations in Chicago

Trump International Hotel & Tower Chicago
Reviewed on Apr 22, 2025


3 Night Romantic vacations in Chicago

Ambassador Hotel Chicago
Reviewed on Apr 23, 2025


Fairmont Chicago at Millennium Park
Reviewed on Apr 24, 2025
4 Night Romantic vacations in Chicago

Fairmont Chicago at Millennium Park
Reviewed on Apr 24, 2025


Trump International Hotel & Tower Chicago
Reviewed on Apr 22, 2025
Top reasons for your vacation to Chicago
- Urban Charm and Skyscrapers: Chicago is renowned for its towering skyscrapers and urban charm, creating a romantic atmosphere for a getaway vacation.
- World-Class Theaters and Museums: Explore the impressive theaters and museums in Chicago, showcasing art, history, and theater productions that cater to all tastes.
- Natural Scenery and Hidden Gems: Beyond the city limits, discover breathtaking natural scenery and uncover hidden gems in charming neighborhoods.
- Iconic Monuments and Vibrant Entertainment Scene: Chicago is dotted with iconic monuments and offers a vibrant entertainment scene that promises endless possibilities.
- Shopping Spree and Unique Souvenirs: Indulge in a shopping spree at upscale boutiques and explore the city's shopping scene for unique gifts and souvenirs.
Book a Package and Save Money on Your Chicago Vacation
A travel package combines flights with hotels or car rental, allowing you to conveniently book everything in one place. It saves you time and effort by eliminating the need to search for separate deals. Plus, it can help you save money by offering discounted rates. Customize your package to suit your preferences and budget with Expedia's price and theme filters.
Looking for a romantic getaway? Chicago is the perfect destination for you. With its stunning skyline, world-class theaters, and breathtaking architecture, you and your loved one will be immersed in a romantic atmosphere. Explore the city's museums, art galleries, and monuments, or simply enjoy the entertainment and scenery. And don't forget about the incredible shopping opportunities. Book your package now and create unforgettable memories together.
How to Save Money on a Vacation to Chicago
- Take advantage of public transportation options in Chicago, such as the CTA buses and trains, to save money on local transport.
- Consider purchasing a Chicago CityPASS, which offers discounted admission to popular attractions like the Shedd Aquarium and the Art Institute of Chicago.
- Explore free attractions in Chicago, such as Millennium Park and the Lincoln Park Zoo.
- Save money on dining by trying out local street food vendors or opting for affordable eateries in neighborhoods like Pilsen and Bridgeport.
- Book your romantic getaway through Expedia's OneKey program to enjoy exclusive discounts and rewards.
Where to Stay in Chicago
When it comes to planning a romantic getaway in Chicago, you'll be delighted by the diverse neighborhoods that offer unique experiences. From the charming streets of Lincoln Park to the vibrant nightlife of River North and the upscale shopping of the Magnificent Mile, Chicago has something for every couple seeking a memorable vacation.
- Downtown Chicago: Experience the awe-inspiring skyscrapers, stunning urban architecture, world-class museums, scenic river views, captivating theater performances, and vibrant art and entertainment scene. With its picturesque scenery and iconic monuments, Downtown Chicago is the perfect destination for a romantic getaway.
- The Loop: Immerse yourself in the urban charm of The Loop, featuring impressive architecture, renowned museums, captivating art, towering skyscrapers, exceptional theater performances, and a plethora of entertainment options. Indulge in shopping, dining, and explore the rich history and monuments, making it an ideal choice for a romantic vacation.
- Near North Side: Discover the allure of Near North Side with its breathtaking skyscrapers, urban ambiance, magnificent architecture, scenic views, world-class museums, picturesque river, captivating art, shopping havens, charming lakeside, and delightful dining options. This area offers a perfect blend of romance and exploration for a memorable getaway.
Explore the best places to visit in Chicago
Chicago (and vicinity) offers a vibrant and romantic atmosphere for a getaway vacation. With its iconic skyscrapers, world-class theaters, stunning architecture, and renowned museums, there's plenty to explore and admire. Take a romantic stroll along the Lakefront Trail or enjoy a peaceful picnic in Millennium Park. Indulge in the city's vibrant art scene and catch a show or visit the numerous art galleries. End the day with a romantic dinner at one of Chicago's top-rated restaurants or explore the lively nightlife. Don't forget to explore the city's shopping scene for unique gifts and souvenirs.
- Six Flags Great America: Experience the thrill of roller coasters and live music performances at this popular theme park. Enjoy the scenic views of the lake and forests while birdwatching. It's a family-friendly destination with plenty of shopping and friendly people.
- Chicago Riverwalk: Explore the beauty of Chicago's riverfront with stunning architecture and skyscrapers. Take a leisurely walk along the river, enjoying the friendly atmosphere and scenic views. You can also go boating or dine at one of the many waterfront restaurants while witnessing breathtaking sunsets.
- Art Institute of Chicago: Immerse yourself in art and culture at this renowned museum. Admire the urban skyline and architectural wonders while exploring various exhibits. From theater to monuments, this museum offers entertainment for all. Don't miss the chance to interact with friendly people who share a love for art.
Best months to visit Chicago
Chicago boasts a year-around average temperature of 51.3°F, peaking at 75.9°F in July, its warmest month, and dipping to an average low of 24.8°F in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.
Month![]() | Temperature (Fahrenheit)![]() | Rainfall (mm)![]() |
January | 24.8 | 52.3 |
February | 28.8 | 49.3 |
March | 38.8 | 69.1 |
April | 50.5 | 92.5 |
May | 61.0 | 104.9 |
June | 71.1 | 103.1 |
July | 75.9 | 101.9 |
August | 74.1 | 101.3 |
September | 66.4 | 84.1 |
October | 54.3 | 82.3 |
November | 41.5 | 86.9 |
December | 28.9 | 65.3 |
How to find a romantic Chicago vacation
How can I find the best Chicago vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Chicago romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.
How can I plan a great romantic trip to Chicago?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Chicago?
Put a price on love with stunning deals for duos starting at just $221. Prices and availability are subject to change. Additional terms may apply.
Can I book Chicago spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
How can I book romantic weekend getaway packages in Chicago?
To book a loved-up break in Chicago, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Chicago with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Chicago romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?
Top Romantic Chicago Hotels

Couples like: adults only property, spa tub, fireplace, romance packages available
Reviewed on Apr 18, 2025

Couples like: full-service spa, couples spa treatments, bar
Reviewed on Apr 23, 2025

Couples like: full-service spa, couples spa treatments, happy hour
Reviewed on Apr 23, 2025
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