One of the many things that makes Chicago* so special is that it is a big city, but it still has a small town feel because of its vibrant neighbourhoods. Our latest travel series, Chicago Neighbourhoods, takes you on a tour of some of the Windy City’s bustling neighbourhoods and hidden gems. You will see some of Chicago’s Bucket List attractions and some that are less well-known but should be on your radar. Mix and match these Chicago neighbourhood guides for your next visit to one of North America’s top destinations for your ultimate trip. Whether you have one day to explore or a week, we’ll share the tips that you need to get the most out of your time there.
First up, North Michigan Avenue, better known for it’s nickname, The Magnificent Mile, is amongst the most popular with tourists. Filled with shops, restaurants, hotels and other attractions, it is a must do if you have never been to the city before and only have 24 hours to explore. The Magnificent Mile’s 13 blocks stretch from Oak Street in the north to the Chicago River in the south, and finally, lakeside to the east.
How you choose to explore Chicago neighbourhoods depends on how much time (and energy) that you have. The good news is that The Magnificent Mile is very walkable. It’s mainly flat and very easy to navigate. If you are directionally challenged, use the Chicago River as your landmark – it is south and if you continue to walk in that direction, you will hit Chicago’s famous Loop neighbourhood.
Now that we have oriented you, it is time to share some of our must-sees on The Magnificent Mile:
Hotels
Yes, you read that correctly. The Magnificent Mile is home to some of Chicago’s most iconic and historic hotels. As an explorer, put these historic hotels on your own “Chicago Bucket List”:
The Drake Hotel: Both Hollywood and British royalty, including Queen Elizabeth II and Diana, The Princess of Wales, slept at this grand hotel. Make reservations for tea to feel like royalty yourself. It is technically in The Gold Coast neighbourhood, but it is Magnificent Mile adjacent, so we are counting it in our must-sees.
Millennium Knickerbocker Hotel Chicago: The Gothic-Revival Hotel, established in 1927 has a storied past. For a brief time, it was the Playboy Hotel. It was also a speak easy run by the Capone family – yes that one.
Park Hyatt: Visit this hotel to enjoy a drink with a view of North Michigan Avenue – it’s just a really nice place to stop and enjoy a cocktail.
Chicago Neighbourhoods: Things to Do on The Magnificent Mile
My number one piece of advice – keep your eyes open. You never know what you are going to stumble upon. During one visit, I walked by a special Friends (the popular TV sitcom) exhibit. Another time, there was a Harry Potter immersive experience. There is always something special that you will find whether it’s a beautiful sculpture, an exhibit or an interesting pop-up store.
Always end with your hotel if it’s close or on The Magnificent Mile. You will be doing a lot of walking ,having that orientation and knowing that you will be able to rest your weary feet before you step out for dinner is a must. Here are some of my favourite things to do:
Shop ’til You Drop: You are in a shopping lover’s paradise. Nordstrom, Bloomingdale’s and Neiman Marcus must visits for luxury shoppers – especially since Nordstrom left Canada. Ulta (fun to visit since the retailer isn’t coming to Canada), Sephora (they carry some lines that we don’t have) and Saks for the bougie makeup maven. Don’t forget the kids – there is a huge American Girl flagship store at Water Tower Place. You will also find a LEGO store at the famous shopping tower.
Abel Arciniega: @tequilagraphics
360 Chicago and TILT: Chicago 360, on the 94th floor of 875 North Michigan Avenue will give you the best views of the city in this particular neighbourhood, but I’ll share an even better destination in another area – you will have to check back for that recommendation.
TILT is unique and fun if you like heights. It’s billed as a ride, but you literally tilt forward more than 1030 feet above the ground. I loved it, but if you are afraid of heights, it may not be right for you. It is fun to do in the evening to see the lights of the city spread out in front of you. My tip – call ahead if it’s a hot day to see if the air conditioning is working – it wasn’t the day that I went and it was stuffy and warm.
Chicago Roastery – Starbucks Reserve: Hear me out – this is an experience not to be missed. It’s not a traditional Starbucks. This is the world’s largest Starbucks. It opened in 2019 and it still has lineups. I recommend going on a weekday afternoon versus on the weekend to avoid standing in line. Chicago Roastery is a four-floor (plus terrace) masterpiece of design. The escalators leading to the second floor are semi-circular – I’ve never seen anything like them. You will find bits of Starbucks’ history, coffee tasting, delicious food options and even cocktails at the Roastery.
The Architecture: Chicago’s skyline is arguably one of the most beautiful in North America. Yes, there are the requisite skyscrapers, but each is beautifully designed and are true architectural feats. They also do not tear down older buildings, so the heritage of the city is maintained.
One of the most beautiful buildings is The Wrigley Building named after chewing gum magnate William Wrigley Jr. It is a stunning masterpiece of Spanish Colonial design and one of the most iconic buildings in The Windy City. Other buildings of note include Tribune Tower, 333 N Michigan Ave, LondonHouse, and yes, even Trump Tower. You can take a walking tour to learn more about the iconic buildings at the Chicago Architecture Center.
Chicago Riverwalk: Another must-do near The Magnificent Mile is Riverwalk. It’s a beautiful 1.25 mile walk along the Chicago. It is a great way to spend a warm summer day. There are many restaurants to enjoy, but take an architectural cruise – it is your gateway to exploring more that the city has to offer and it is something that everyone should do at least once. If you only have time for one tour in Chicago – this is the one to do.
There is so much more to explore like Navy Pier. The next time I go to Chicago, I’ll head there and report back on Streeterville.
Where to Dine on The Magnificent Mile
Chicago has one of the best dining scenes of any destination that you will find and there are no shortage of restaurants on The Mag Mile. Here are just a couple to tantalize your tastebuds with:
Lou Malnati’s Pizzeria (410 Michigan Avenue): You have to try Chicago deep dish pizza at least once, and Lou Malnati’s is a great place to sample it. The personal size is manageable to eat (deep dish is notoriously filling) and they are made from scratch. You will find the restaurant on the exterior of The Wrigley Building.
Coq d’Or at The Drake Hotel: This Chicago fixture opened on December 6, 1933, just after the repeal of Prohibition. It is a warm, traditional restaurant with great food and great service. Since Prohibition is long over, try some of their cocktails or their branded Rye Whiskey to start. The Bookbinders Red Snapper Soup is what the restaurant is most famous for and the recipe has been a staple since the 1930s.
We will be exploring more Chicago Neighbourhoods so that you can plan your ultimate trip!
*Hosted by Choose Chicago – opinions are my own.
