Chicago, the city with the nickname ‘Windy,’ is a vibrant city that provides a beautiful and unique mix of contemporary architecture, history, landmarks, and great eating establishments. Whether you are enjoying the vistas over the shores of Lake Michigan or gazing at the stunning silhouette of the city’s skyscrapers, dining at one of its finest restaurants in the company of your beloved, Chicago is the answer for lovers tired of routine.  

Explore the best couple-friendly Chicago packages on Trekhops.com! Find the best Chicago romantic tour packages and luxurious tours. Discover the best attractions for lovers, as well as special romantic tours, with the best itineraries and luxurious accommodations in Chicago. 

Choose Chicago for a Couples’ Getaway 

Chicago is a city blessed with stunning views, amazing places of interest, and a wealth of culture. Everyone knows that art, gourmet, and nature are the biggest attractions for lovers, and Chicago has all these things for a couple. Its façade has retained the old-world charm while inside, it boasts of all the modern amenities, thus making it a romantic Chicago tour. And sipping cocktails, most notably at a candlelight dinner while strolling through the city skyline or taking an incredible boat ride on the river, makes Chicago the best destination for couples who want a magical feel for their vacation. 

Best Romantic Chicago Tours for Couples 

If you’re going to stay in Chicago for the weekend or even several days, several tours should contribute to an interesting stay in this city nicknamed the Windy City. Below are some of the best tours for couples that capture the magic of Chicago:  

• Chicago Architecture River Cruise: Chicago is a city for lovers of architecture and one of the most beautiful ways to look at the city is from the boat on the Chicago River. This is a luxury tour in Chicago for you and your partner to take a brief serene on the Chicago River, taking you past major buildings such as the Willis Tower and the Tribune Tower. Many boat cruises have an informational component, such as an expert giving information on the history and architecture of the city’s skyline. If you are interested in more intimate, you can go looking for a sunset or evening cruise so the lights from the city will be reflected to the waters making it more romantic. This is one of the most beautiful Chicago tours that any romantic couple with a desire to explore history would like to do.  
• Helicopter Tour over the City: For couples who love the feeling of the heart racing, there’s no better place to find this feeling than flying in a helicopter around Chicago. During the flight, visitors can see impressive sights of the lake, the Millennium Park, the Navy Pier, and downtown through the glass bottom of a helicopter. Some of the unique luxury tours in Chicago include private helicopter tours because you both can share thrilling experiences. This is not only an exciting thing to do but proves to be very romantic. Wait to see the sunset on the horizon and the lighting turn everything yellow. As for honeymoons in Chicago, this is a unique chance to look at the city from a very different angle.  
• Private Food Tour in Chicago’s Neighborhoods: Chicago boasts of some of the finest foods across the United States, and having a private food tour gives couples a chance to taste some of the best cuisines. Deep-dish pizza pairs perfectly with Chicago and the celebrity chefs, local Magazine Street restaurants, or a small Italian restaurant hidden in Lincoln Park or West Loop, a wonderful Chicago food tour. Many Chicago romantic tours have a flexible meaning that you can tailor your day’s dining in a certain way. Whether your interest is fine dining restaurants, fast food, or ethnic food, which is popular in Chicago, you can anytime plan your dinner date. 
• Art Institute of Chicago Private Tour: Art lovers should consider spending an evening on a private tour of the Art Institute of Chicago, because it is one of the biggest and best art museums in the world and contains pieces by such artists as Van Gogh, Monet, Picasso, and many others. It is especially beneficial for couples to take a private tour because they can always take time to appreciate art, which they like the most. This luxury tour in Chicago is especially suitable for couples who would like to do more than simply sightseeing. There is even the opportunity to end the day with a walk at Grant Park nearby or taste exquisite meals at any gourmet restaurant of choice for a full art and gastronomy day. 
• Chicago Segway Tour for Couples: If you and your partner are not very active, but still want to have fun and see as much of the city as possible – rent a Segway. This is especially recommended when one wants to cover a number of sites within a relatively short space of time, for example, Millennium Park, Grant Park, and the Museum Campus, not forgetting the beautiful Chicago shoreline. These guided Segway tours are usually centered on the history and the culture of the city. Therefore, it would be perfect for couples who love the educational kind of tour. This is among the more exotic romantic vacation activities in Chicago, as well as an entertaining and informative source of history on the city. 

Luxurious Chicago Tour Packages for Couples 

Spending a romantic time in Chicago is not only about fancy plates and exclusive guided excursions but also about luxury. If you want to have a explore Chicago in terms of luxury, here are some of the finest luxury tours to take in Chicago that offer that classy touch.  

• Private Yacht Cruise on Lake Michigan: To get a taste of high-end, personalization, and exclusivity, then take a private yacht cruise on the shores of Lake Michigan. Most luxury tour operators specialize in tailor-made programs for sightseeing with a private cook, candlelight dinner, champagne breakfast, etc. A cruise to and through the great Rochester’s Lake gives you uninterrupted sightseeing of the Chicago skyline and is ideal for a romantic weekend with your special somebody. It is perfect for a romantic honeymoon or just a Chicago romantic getaway that is primarily focused on leisure and a polished atmosphere. 
• Luxury Hotel Packages with Spa and Dining: Most of the best hotels in Chicago have incorporated luxury packages such as relaxing spa treatments, fine dining, and private tours of the city. Hotels that offer couples the best accommodation, and exceptional complementary packages, which may comprise cooking classes, wine tours as well as helicopter rides, are the most affordable. By booking these packages, the couples get a chance to enjoy the elite services offered by Chicago’s hospitality industry. 
• Romantic Dinner Cruise on Lake Michigan: One of the most romantic ways to spend time with your loved one is dinner on a ship. Some firms take couples for dinner cruises on Lake Michigan, and they get to enjoy well-cooked meals, and live entertainment through musicians and dancers as they watch the beautiful view of Chicago’s skyline at night. This is one of the greatest Chicago romantic tours and must be done on an anniversary, engagement or even a date. 

Best Time to Visit Chicago for Couples 

Chicago tours that are most suitable for lovers can best be done in spring and autumn, preferably from April to June as well as from end of September up to October. These months are comparatively cooler, and the warmer climate has turned gardens and parks of the city into riot of colors. Autumn is a good time of the year for couples as it’s not as hot as summer, and there are not a lot of tourists around.  

High season is in the summer, which lasts from July to August, because the climate is still tropical and it is the time of festivals, however, it will be crowded and costly. Winter is really cold most of the time, but there is something amazing about it, especially when the city is covered in lights and decorations for the holidays. Besides summer, winter could also be a little bit romantic, though cold and windy, it is good for walking around museums, visiting different kinds of attractions, warm yourself with hot chocolate in the delicious coffee shop. 

Tips for Planning the Perfect Couples’ Getaway in Chicago 

• Book Early: Chicago is an attractive tourist location throughout the year, thus, when planning for your tours, hotels, and restaurants, make sure to make your bookings early, especially during the busy season.  

• Plan Around Festivals: Chicago’s annual events include the Taste of Chicago, the Chicago Blues Festival, and the Chicago Air and Water Show. It can provide an additional experience to your trip, but some of them can attract a lot of people, so be ready for it.  

• Opt for Private Tours: For a more intimate experience, choose private tours or small group excursions. This not only allows you to explore at your own pace but also provides personalized service and a more romantic setting. 

• Indulge in the City’s Culinary Scene: Chicago has perhaps one of the best food markets in the whole of America, so confirm seats at some of the best restaurants. Whether you’re heading out to enjoy a candlelight dinner with your partner while watching the setting sun over the state or just grabbing a burger and pizza with friends at some chic restaurant or bar, food is a memorable part of your Chicago encounter.  

Conclusion 

Chicago offers a couple something for everyone and the adventurous that develop new passions among them. From the imposing skyline and colorful districts to upscale sightseeing and personal excursions, the Windy City has everything any couple could desire on vacation. For easy booking and planning, visit Trekhops.com to make the most of your romantic getaway in Chicago.  

Whether you are planning a weekend trip or a more leisurely luxury vacation, these romantic getaways will make your trip full of love, wonderful and inspiring discoveries.