This is one of our FAVORITE places in the city! That’s why we decided to get married here! The drawing room is cozy and laid back, the Game Room has hours worth of activities, and the Cherry Circle Room has amazing food and cocktails in a truly unique setting!
If you haven’t been, make sure you checkout the old Marshall Fields’ building and the grandeur of department buildings. The architecture is stunning, and make sure you swing by the 7th floor to see the Walnut Room. While you’re there, you might as well pick up some Frango Mints.
Within walking distance of the Chicago Athletic Association, the AIC is one of the world’s most famous and robust art museums. The Impressionist collection is extraordinary. Ferris Bueller fans should make sure to stop and stare at Pointillism’s masterpiece, A Sunday on the Island of La Grande Jatte.
One of the country’s most important contemporary art museums, exhibits are constantly changing. Even if contemporary art isn’t your thing, the building is impressive, and the views from the terrace are spectacular. Marisol on the ground floor is a wonderful new restaurant.
If weather permits, the Ribbon is a unique skating experience within walking distance of the Chicago Athletic Association. True to it’s name, you skate around a ribbon like stream of ice. Don’t mistake this for the traditional ice rink across the street from the Chicago Athletic Association, keep going closer to the lake. Fun fact, Kay and Kevin came here on their fourth date, and Chicago Athletic Association after for dinner and drinks. It was on this date that both realized they really liked each other and the other could be ‘the one!’
Directly across the street from the Chicago Athletic Association, this sculpture, better known as ‘The Bean,’ by Anish Kapoor is Chicago’s most popular public piece of art. Great photo ops abound!
The heart of Chicago’s extraordinary culinary scene! You can’t go wrong with anything on this street from the best burgers period, to Michelin star set menus. Expect long waits but well worth it. Some of our favorites are individually called out in this recommendation list. A unique spot to the far west is Kaiser Tiger. If you’re interested in trying your hand at curling head here. Just get there early because spots are given out on a first come first serve basis.
You can’t come to Chicago without trying a Chicago style hot dog; remember NO KETCHUP!
The.Best.Restaurant.In.Chicago.Period! Try and get reservations early. If you can’t book a reservation in advance, there is standing room only at the bar. Worth standing and eating!
The most beautiful spot in all of Illinois! Makes sure you get a glimpse or two before you leave!
There’s no better place for live music in all of Chicago! The Green Mill opened in 1907, and has had a long sordid history. A go-to hangout for Al Capone and other mobsters, it still has the ‘get-a-way’ trap door behind the bar for when the cops came. There is a cover charge but well worth a visit! This was another early date spot for Kay and Kevin.
The Drifter is Chicago’s only true speakeasy. This bar remained open during prohibition, and continues the tradition today with a door behind a bookcase in the basement, and live entertainment every night. Great spot for cocktails as well!
If you’re looking for an AMAZING burger, look no further! This upscale diner always has a wait but it is worth it when you try their famous double cheese burger. This burger is considered one of the best in the country. If there’s a wait, go next door to Lone Wolf, and enjoy a delightful cocktail while you wait.
A rare gem on Michigan Avenue, this Bib Gourmand recipient has an impressive wine list and wonderful plates that can and should be shared.
A Chicago institution, this Loop restaurant as been in business since 1935. It’s very cozy and offers straightforward classic American fare.
This is a trendy spot on Michigan Avenue, and just steps from the Chicago Athletic Association. This cozy gastro pub offers great food options and a nice ambiance.
‘On State Street that great Street...’ - Frank Sinatra’s Chicago. This was the heart of Chicago’s entertainment for much of the 20th century. It’s now home to a lot of shops and where Macy’s State Street and the Chicago Theater are located. If you walk North to Walker Drive you’ll come to the famous Chicago River.
This is THE steak place in Chicago. A more expensive dinner option but if you’re looking for steak in Chicago this is it.
One of Chicago’s most beautiful hotel lobbies! Built in 1871, and burnt down 13 days later by the Chicago Fire, the current hotel re-opened its doors in 1925. Absolutely worth a visit to see the lobby, and why not stop and have a drink or two in the lobby bar. This is a short walk from the Chicago Athletic Association.
We promise we’re not recommending this to nudge you toward our registry. This is Bloomingdales only store in the U.S. dedicated to their home goods, and the store is housed in is an amazing Arabian style old theater.
Just a 5-10 minute walk from the Chicago Athletic Association is the iconic Chicago Theater on State Street. This is a quintessential photo opp while you’re in Chicago.