Where to Propose in Chicago
Chicago Proposal Ideas
Chicago is a vibrant city of opposites; cutting edge modernity alongside passionately preserved history, and luxurious indulgence colliding with hard working realism. From the glass-like beauty of Lake Michigan to the architectural glamour of the Magnificent Mile, there are plenty of memorable places to propose to your girlfriend in Chicago. Here are some ideas for iconic proposal locations and places where you’ll get a great view of the city while you pop the question, as well as green spaces for a more private proposal.
Iconic proposal locations in Chicago
One of the best known icons of Chicago has to be the Wrigley Building, a sparkling white office block located on Michigan Avenue on the north bank of the Chicago River which has become the symbol of the city. If you’re thinking of proposing in front of the Wrigley Building, wait until nightfall so you can take advantage of its spectacular lighting.
Another symbolic location with fabulous night time lighting is the Buckingham Fountain in Grant Park. Give a decadent French flavor to your proposal as the fountain, built in 1927 in the rococo style, was inspired by the fountains at Versailles, near Paris. It is one of the largest fountains in the world and operates from April to October. There is a water show every hour, on the hour, between 8am and 11pm, and at night the show is timed to music and lights.
The Chicago Water Tower is an unusual choice if you’re looking for a taste of old Chicago. One of the few buildings to survive the Great Chicago Fire of 1871, this beautiful landmark is located on the Magnificent Mile, and you can use the City Gallery exhibitions it contains as an excuse to visit it.
For a more modern location of significance in Chicago, check out Cloud Gate, affectionately known as The Bean, located in Millennium Park and completed in 2006. Cloud Gate offers a unique mirror image of the Chicago skyline, and when you walk underneath it has unique reflective properties, ideal for getting some unusual engagement shots once you’ve popped the question.
Finally, the Field Museum of Natural History might not seem like the obvious place to propose, but they do have a very novel proposal package which might be worth considering. At the updated Grainger Hall of Gems, which houses diamonds and gems from all over the world, you can place your engagement ring inside a dedicated exhibition case within the gallery with a personal message and special lighting. You can then celebrate at the museum with a champagne toast.
Proposing with a view of the city
There’s no better view of Chicago, and a lot more besides, than from the Skydeck at the top of the Willis Tower. You can propose with the city literally at your feet if you step out into one of the glass balconies that extend from the top of the third tallest building in the world, and on a clear day you’ll have a view that includes four states. Sunset is a fantastic time to visit the tower, but don’t forget it closes at 8pm in the winter and 10pm in the summer. Contact the Skydeck team in advance if you’d like to make special arrangements for your proposal.
Those of you that aren’t too keen on heights don’t need to go to such lengths to get an amazing view of the Chicago skyline. North Avenue Beach is a fantastic proposal location as it gives a beautiful view of both the city and Lake Michigan, especially if you venture out onto one of the beach’s piers. Another beach with superb views is Ohio Street Beach, which faces North rather than East as it juts out into the lake.
Green spaces to propose in Chicago
Lincoln Park is the largest park in Chicago, following alongside the shore of Lake Michigan. While there are plenty of beautiful locations to propose within the park, many couples are attracted to the Lincoln Park Zoo, which is one of the oldest zoos in the country and has a particular charm, especially if the two of you are animal lovers. The bridge over the South Pond at the zoo provides a secluded and peaceful place to propose. If you’re planning a Spring proposal, consider the Alfred Caldwell Lily Pond, also within Lincoln Park, a beautiful example of prairie-school landscape architecture.
The Chicago Botanic Gardens are an excellent choice for an outdoor proposal. Whatever season you choose you can be sure to find beautiful locations within the extensive gardens. The Japanese garden is a romantic choice, or Evening Island is spectacularly lit every night at twilight and can be accessed by two bridges over the water.
Romantic Restaurants in Chicago
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.
Romantic Activities in Chicago
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
Where to Stay in Chicago for Your Proposal Trip
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.
