If you and your sweetheart will be spending time in the windy city, Chicago sightseeing tours are ideal for a memorable retreat. Even if the two of you live in the area, taking a tour is a fun way to spend the day. Whether you have an afternoon or a month long vacation to spend wandering around the city, there is a tour to match the time you have available. To view the many popular Chicago attractions, take a bike, boat, or even a trolley. The ability to take many of the tours during the day or at night lets you see the city of Chicago in a new light.

Hop-On Hop-Off Trolley Tour

Taking a trolley to see Chicago attractions gives both of you the opportunity to create personalized Chicago sightseeing tours to match your interests. Ride on one of the many trolleys through the city until you see a sight that interests you. Then, get off and take as much time as you want exploring the area. When you are ready, simply board the next trolley until you have seen all of the fantastic sights in Chicago. Things to do with your sweetie while on a trolley tour can include stops at fun locations such as The Adler Planetarium, The North Pier, and The Shedd Aquarium as well as other historic buildings. One such tour called the Hop-On Hop-Off Trolley Tour, gives you the benefits of a guided tour for all the must-see Chicago attractions while still allowing for lots of time to spend shopping, having lunch, and seeing what you want to see rather than having to sit through the things you don't want to see.

Get Spoiled The Old-Fashioned Way

In Chicago, things to do while in the city can include fun and unusual Chicago attractions that you do not normally get the chance to do. To spoil each other, consider an afternoon of shopping at the city's hottest designer clothing outlets. There are more than 120 different designers with outlets in the city including Calvin Klein, Dooney & Bourke, Kenneth Cole and Ralph Lauren. Most of them can be found all in one spot located just outside of Chicago. Things to do after the two of you are done shopping can include an evening at one of the Chicago attractions sure to make the day memorable.

The Medieval Times Castle, Schaumburg Castle, is a fantastic spot to enjoy the life of a medieval king and queen. The evening starts with a medieval-style meal served by 'serfs' while watching time period recreations of games such as jousting. When you are finished your meal, retire to the 'Knight's Club' to enjoy some 'mead' and dancing.

The Chicago Skyline At Its Best

For the most romantic evening in the city, take an evening cruise on the waters of Lake Michigan and see the breath-taking skyline of Chicago. Sightseeing tours at night let you see how differently the skyline looks when it is highlighted by the colors of the setting sun reflecting off the water. This gives you an entirely new view of places such as the Sears Tower, the Chicago Harbor Lighthouse, the Hancock Center, and the Aon Center.

One of the most romantic Chicago sightseeing tours like this includes the Spirit of Chicago Dinner Cruise. A candlelight four-course meal is served while the boat travels along the outside of the city. The rest of the evening includes live musical performances, drinks on the deck, dancing, and gazing at the spectacular lights of the city.

Chicago sightseeing tours are perfect for spending time together in the city. Things to do in the city can be virtually anything your hearts desire. From fun shopping sprees and visiting historic attractions to an evening of fine dining, the mix of Chicago attractions provides the perfect opportunity for the two of you to enjoy each other's company.