Chicago has a wide range of hotels to suit all tastes and budgets so you’re sure to find the perfect accommodation for your stay in the Windy City. Here are a selection of boutique, luxury, and historic hotels to inspire you.

Boutique hotels in Chicago

Chicago is well known as an environmentally conscious city, so a stay at its first downtown eco-friendly boutique hotel Hotel Felix could be the perfect match. Designed to create a soothing energy and refreshing atmosphere, Hotel Felix features white marble columns and relaxing water features behind its 1920s facade. Another new boutique hotel that aims to balance nature with new technology in a zen-like environment is the Dana Hotel and Spa, located in River North, alongside a host of fascinating art galleries.

If you’re looking for boutique hotels near to Lincoln Park Zoo, or close to Oak Street’s Boutique Row if you’d like to do a little post proposal shopping, Hotel Indigo is a calm and contemporary retreat from the bustle of downtown, and the Public Chicago is a stylish minimalist hotel. Alternatively The James Chicago is just a few steps from the Magnificent Mile, and is very convenient for Millennium Park. The brand’s handcrafted and relaxed charm provides guests with what they describe as a ‘luxury liberated’ experience.

Luxury hotels in Chicago

If you really want to splash out and spoil your soon-to-be fiancée, Chicago has plenty of upscale luxury hotels to choose from. The Peninsula Chicago is an elegant five star hotel that prides itself on its impeccable Hong Kong style service and is located on the Magnificent Mile itself. The spacious rooms and suites offer a contemporary feel with classic touches.

For something truly modern why not try the brand new Trump Hotel Chicago, which features bold contemporary design in stainless steel and glass. All the guestrooms have floor to ceiling windows that give spectacular views over Chicago and Lake Michigan, and include every possible luxury. Finally the Ritz-Carlton, which is located high up over the Magnificent Mile in Water Tower Place is an extravagant hideaway, also with fabulous views.

Historic Hotels in Chicago

When we think of romance we often think of older, historic hotels that have more of a story to tell. If you’re looking for a hotel with character and charm check out the Silversmith, an Arts and Crafts style hotel which is conveniently situated for the Magnificent Mile, Navy Pier, and the Sears Tower. Alternatively why not book into The Drake Hotel at East Walton Place, a magnificent hotel built in 1920 in the Italian Renaissance style? If you want a real taste of old Chicago, The Drake is the place to be.

Booking a table at a great restaurant is a superb way to celebrate your engagement, and you can always pop the question over dinner if your original proposal plans don’t quite work out. Whether you like American, French, Italian, or Asian cuisine, here are some possibilities that are sure to impress your bride-to-be.

Everest is a very romantic destination for a post proposal dinner. Located on the 40th floor of the Chicago stock exchange the celebrated chef J. Joho produces fabulous French cuisine accompanied by an excellent wine list.

Crofton on Wells is a well established restaurant in the River North area that serves sophisticated seasonally inspired American cuisine at very reasonable prices.

The Signature Room on the 95th floor of the John Hancock Center is a real treat, not least for the fabulous view while you eat. The wooden art deco interior gives it an intimate feel and the menu is all American.

Alinea is a contemporary restaurant at the forefront of progressive American cuisine and is located in the Lincoln Park area of the city. The 23 course tour menu can take up to four hours and will be filled with gastronomic surprises and unconventional eating methods.

Sunda is one of Chicago’s most popular New Asian restaurants combining flavors from East and South East Asia. Located close to the Magnificent Mile the designer interior adds to the experience and the dishes are designed for sharing.

Piccolo Sogno, translated as Little Dream stands out among an array of excellent Italian restaurants in Chicago. Located in the River North area its rustic regional homemade Italian dishes served in its cozy dining room make it a perfect place for a romantic dinner for two.

Make sure you maintain the romantic mood on your proposal vacation by having a few romantic ideas up your sleeve. The weather in Chicago can be unpredictable so here are a handful of both indoor and outdoor romantic activities in the city.

• Walk hand in hand along the lakefront path next to Lake Michigan
• Visit one of the city’s famous jazz clubs such as the Green Mill Jazz club
• Take a boat ride out onto Lake Michigan
• Ride the Navy Pier Ferris Wheel and watch the fireworks
• Take a carriage ride through the streets of Chicago
• Stroll around the Chicago Art Institute
• See a show at Chicago’s bustling and diverse theatre district