Post Updated March 2021
My husband Robin and I visit Chicago several times a year for work. We always have an excellent time exploring the city, enjoying the art and culinary scenes, and appreciating the unique and impressive architecture. During recent visits to the Windy City, we’ve stood front & center to see Tiësto live after being a fan of his music for more than 15 years, we’ve eaten at some of the best Michelin Star restaurants in the country located in Chicago, and we’ve explored some of the nation’s best museums. We passed through Chicago during our honeymoon and on our way to Europe for the first time a few years ago, and the very first year we were dating, I gave Robin concert tickets to see The Legend of Zelda Symphony Orchestra for his birthday.
It’s safe to say that this city holds lots of happy memories for us, which is why I’m so excited to share more reasons to love and visit this iconic American city!
No matter what we’re doing when we’re in the city, we always have a wonderful time discovering new things to do. Whether we enjoy a new museum or art installation, relax at one of the city’s world-class day spas, or sail on nearby Lake Michigan, it’s an exciting place with so much to do.
Where to Stay in Chicago
Chicago has many attractive and impressive hotels, and we’ve stayed at a number of them. Unfortunately, there will always be some flops in a large city, which means many of the places I’ve stayed in the area I’ve never written about because I wouldn’t recommend them. Below are my tried and true favorite hotels in the city. Each offers many things which are unique to the property that can’t be found anywhere else in the world, and all of them, of course, meet the high standards of my luxury travel series.
The Fairmont chain of hotels is known worldwide for its incredible luxury offerings, posh surroundings, and gorgeous decor. This hotel’s luxury spa, mySpa, is one of the best in all of the city, and the location makes visiting all of Chicago’s significant landmarks very convenient. The views of the harbor from our most recent visit were breathtaking, even in the rain. Fairmont Chicago is also home to Columbus Tap, one of our favorite places to eat in the city.
Kimpton Hotel Monaco
Our first experience with a Kimpton hotel was during our Scottish anniversary trip during the last leg while we were in Glasgow. We loved the incredible service, fantastic accommodations, fantastic European spa, and unmatched hospitality. When we visited Chicago during our most recent trip, we wanted to experience another hotel. I’m happy to report that this hotel was even better than the one we loved in Glasgow and had some of the friendliest staff we’ve ever encountered.
Our room had a fantastic window bench with a great view of the Chicago River, along with a relaxing rain shower, king bed, and more which made us feel right at home.
The Peninsula Hotel
We’ve stayed at the Peninsula Hotel several times during our visits to Chicago and have loved every moment of it. The hotel is an oasis of tranquility and elegance in Chicago, and the staff are some of the most attentive we’ve ever experienced. The hotel has an entire floor dedicated to shopping without even having to leave the hotel. The staff are more than happy to arrange travel itineraries, pick up purchases from shops on the Magnificent Mile, and arrange transportation to and from the airport and around the city. If you’re looking for luxury and convenience, the Peninsula Hotel is an excellent choice.
This beautiful Art Deco hotel is in the Gold Coast neighborhood and has spacious, metallic gold accents, large marble bathrooms with rain showers and deep soaking bathtubs, and one of the best locations in the city. Their restaurant, Somerset, was excellent as well.
Where to Eat
Chicago is one of the best cities in the United States for food, right alongside Los Angeles and New York City, so visitors can find everything from fine dining and exotic cuisine to hole-in-the-wall type places that serve American comfort foods. Here are some of my favorite places to eat in the city.
This incredible Michelin Star restaurant is one of the best dining experiences in the city and some of the most thoughtfully presented food I’ve ever had the pleasure of enjoying. Book a few weeks in advance to reserve your spot, as walk-ins aren’t available, and the bookings fill up very quickly. They can accommodate dietary restrictions and allergies with at least 72-hour notice.
Beatnik on the River
Located along the Chicago River, this is our favorite lunch spot in the summertime. Reserve a table outside by the river for great views and a tranquil atmosphere of ferns, philodendrons, and other plants at this Mediterranean fusion restaurant.
Located inside Fairmont Chicago Millennium Park, this elevated gastropub serves next-level comfort food like fresh and colorful crudités, charcuterie, salads, soups, and sandwiches. We were enamored by the lovely copper, rust, and brown decor as well!
Eddie V’s Prime Seafood Restaurant
This romantic seafood restaurant has some of the finest seafood in the midwest and the most incredible waitstaff we’ve encountered in the Windy City, which is saying something. I recommend setting up a reservation a few days in advance.
This cozy restaurant is the perfect spot for an intimate dinner, right in the heart of the Gold Coast district, around the corner from the Viceroy Hotel. We loved their truffle fries, tuna tacos, and kale & avocado salad.
This darling Italian-influenced restaurant has some of the best Italian food in the midwest, with plenty of pescatarian and gluten-free food options that will transport you directly to the Mediterranean.
RL (Ralph Lauren) Restaurant Chicago
This sophisticated dinner spot is entirely outfitted in Ralph Lauren home decor as an extension of Ralph Lauren’s Chicago flagship store. Be sure to make reservations at least a day in advance, as walking into the restaurant is usually impossible.
This spy-themed bar and restaurant is unlike anything else in the city. Not only is the entrance a bit hidden, but agents must pass a series of tests to ensure they’re not double agents to gain access to this spy-only bar. Prepare for great food, fun games, and many interesting memorabilia from famous spy movies and world events.
has been repeatedly voted the best Chinese food in all of Chicago, and I can definitely see why. The atmosphere was as though we had been transported to an imaginative, exotic location somewhere in China. The staff was cheerful and kind, and the menu had something for absolutely everyone.
Located inside the Viceroy Hotel, this Art Deco restaurant has a fantastic brunch spread, with both indoor and outdoor dining, an extensive bar, and plenty of delightful flavors to wake you up and send you on your way to your next adventure.
The Hampton Social
It just might be one of the cutest, most instagrammable restaurants in Chicago, and the food is incredible!
Wildberry Pancakes & Cafe
has been voted the best brunch in all of Chicago for a few years in a row, plus it has thousands of stellar reviews, so we just had to check it out! I ordered a veggie omelet with a gluten-free berry pancake, and it was incredible! There was an hour to two-hour wait for brunch, so be sure to call in advance and put your name in (they will text you 5 minutes before you need to be there) to avoid standing in a line for hours.
is my favorite pizza place in all of Chicago for incredible, Chicago-style deep-dish pizza, and they even have gluten-free options! Plan to wait 45 minutes to an hour for a deep-dish pizza to cook, or call ahead and pick it up!
is my new favorite place to grab a fresh, locally sourced salad. The prices are great, the portions are massive (I ate salad for two consecutive meals after coming here because I had so much leftover!), and you can either order off the menu or customize your own. They have lots of vegan and non-vegan options for every diet.
Margeaux Brasserie at Waldorf Astoria Hotel
It offers fun, fresh French fare inside a stunning, 1920s inspired atmosphere and has an incredible drink selection. I highly recommend the Salade Niçoise, Warm Camembert Truffle Baguette, and Pomme Purée. They’re all so tasty and satisfying! You can explore their unique menu here.
The Milk Room
Robin and I had drinks here, and the atmosphere was just incredible. They create experimental drinks and put modern spins on traditional drinks, and the bartenders are excellent at their craft. I won’t spoil this place by putting up any photos; you’ll have to explore it yourself; you won’t regret it.
The Violet Hour
A hidden entrance covered by a changing mural and a single bulb makes it difficult yet rewarding to find this place. We went looking for it without GPS and celebrated with an award-winning cocktail when we found it!
Stax Cafe and Eggy’s were two other fantastic places to grab a quick breakfast or brunch that we’ve had in the past and loved. Both can have long waits, so be sure to call in advance and add your name to the list to avoid the lines.
Summer House Santa Monica
This California-inspired restaurant has some of the best food & drinks in the city, particularly if you have a special diet, can’t eat gluten, or have food allergies. Their staff is so careful and thoughtful about preventing cross-contamination, and the food is outstanding. Plus, it’s like being transported to California, so it’s like a vacation in a vacation!
What to Do in Chicago
There is SO much to do in Chicago, no matter your age, activity level, budget, or interests. In any city that offers it, I always recommend getting a CityPASS, a convenient way to save money on all of the city’s major attractions. In Chicago, the CityPASS saves you 51% on admission and gives you the ability to skip the lines at the Shedd Aquarium, Adler Planetarium, or The Art Institute of Chicago(pictured below), The Field Museum, Museum of Science and Industry or the 360 Chicago Observation Deck, and the Skydeck Chicago.
AIRE Ancient Baths is a cross between an incredible day spa and bathing in an incredible, serene, subterranean cave. This oasis is the perfect way to unwind in the busy city, and it’s consistently voted one of the best experiences in the city. Check out my video tour of AIRE below, and read my full guide to this one-of-a-kind experience here.
Chicago has no shortage of museums, and in addition to the museums listed above, I’ve loved visiting the Museum of Contemporary Art, Museum of Contemporary Photography, National Museum of Mexican Art, International Museum of Surgical Science, National Museum of Puerto Rican Arts & Culture, and the Renaissance Society, which is completely free.
In addition to CityPASS activities, there are many tours from architecture or food and drink tours to more sordid and supernatural tours. We enjoyed a Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. It was a fantastic way to learn about the history of Chicago, its unique buildings, the history of architecture, and its influences on the midwest. It’s also a great way to see the city from a new perspective because everything looks completely different from the water, and we were able to see the backs of the buildings along the River Walk from a new perspective.
If you’re looking for something more adventurous, there are two huge, public rock climbing walls in Maggie Daley Park, or you can go skydiving over Lake Michigan with Skydive Midwest. You can also find places to rent paddleboards, jet-skis, and even parasail or charter a sailboat out on Lake Michigan, which I always recommend to people, especially those who live outside the Great Lakes Basin.
Next time we are in town, we want to check out some of the French cooking classes offered in town and take a mixology course at The Violet Hour to learn to make our own mixed drinks. Chicago offers endless class options from chocolate-making and cooking for newlyweds to wine-making, wine, food pairing courses, and even free photography courses. If you search just about anything and “Classes Chicago,” you’re bound to find some wild and interesting classes Chicago has to offer.
Chicago is one of the best places in the United States to go shopping because they have unique flagship stores, high-end and luxury shops, artisanal boutiques, handmade shops, and so much more along the Magnificent Mile and beyond. I ordered my dress for our anniversary celebration from the BHLDN store in Chicago, and the staff treated me like a princess the entire time! Shopping along the Magnificent Mile isn’t just for the wealthy, be sure to pop into luxury stores like Dior, Gucci, and T.Co to check out their artistic displays and browse. The workers don’t want you to be afraid to visit, even if you don’t plan to spend anything.
Check out Fashion Outlets of Chicago, located near O’Hare airport, for unbeatable shopping and the midwest’s only luxury outlets, featuring Gucci, Ralph Lauren, Prada, Moncler, Jimmy Choo, and so many more. Watch my haul video from Fashion Outlets of Chicago here, and read my post about the great reasons to shop there here.
Navy Pier is definitely a can’t miss part of Chicago. This is where the newly remodeled Ferris Wheel is, and where you can find fun, food, rides & games, fireworks, events that are free and open to the public, exhibits, tours, and so much more. There’s even a beautiful botanical garden inside. The activities and events happening on the pier change daily and weekly, so be sure to check out the schedule of events here before your trip to best plan your time here.
If you enjoy baseball games as much as my husband and I do, you can’t visit Chicago without seeing the White Sox play! We went to Guaranteed Rate Field during our last visit to watch the Chicago White Sox play against the Cleveland Indians, and it was a great time.
Millennium Park, home of the famous, mirrored “Bean,” always has something going on. While we were in town the last time, a Jazz Festival and wine tasting event was happening, and the most recent time, there was a gourmet food festival happening.
We once visited for Spring Awakening, which is one of many concerts in Chicago that weekend. Concerts, shows, and performances are always going on, and there is always something exciting happening in town, so be sure to plan your visit around something exciting. The first time I ever came to Chicago was with my husband for his birthday to see The Legend of Zelda Orchestra. I’d surprised him with tickets, and it was just such an incredible experience. I’ll be coming back a bit early from Paris Fashion Week this year and heading straight to Chicago to see my favorite Korean Pop group BTS performing in Chicago for the first time, and I am so excited!
Chicago has incredible nightlife with several clubs, bars, pubs, shows, and open late things. Like most big cities, there’s always something to do when the sun goes down, and Chicago certainly has some interesting and unique things in the nightlife sphere.
Instagrammable Spots & Famous Landmarks
Centennial Ferris Wheel
DuSable / Michigan AvenueBridge
The Art Institute of Chicago
The Bean in Millennium Park
Willis Tower Observation Deck
Magnificent Mile Luxury Shops
Getting Around Chicago
We drove to Chicago from Detroit, but we parked our car with the valet and hiked around town on foot once we arrived. The city has an awesome bike-sharing program where you can pay a flat fee for daily rentals or rent by the hour and drop bikes off in other locations around town. You can also use Uber or Lyft to get around cheaper than taxis and tell you the total fare beforehand. There is also a subway system and an above-ground train called the “L” to get you wherever you need to go.
Parking in Chicago can be a pain, but it doesn’t have to be. We usually park our car with the valet at our hotel, so we don’t have to worry about it being accidentally damaged (street parking can be scary!), and take Ubers around town. There are also parking garages around town and guarded parking lots for day parking. Parking can run from $25-$75/day, depending upon how you choose to park.
Use the SpotHero app, and you can find parking for up to 80% off around the city, which is perfect if you’re planning to drive your own vehicle around town.
Wherever you park, be sure to keep your valuables out of sight and locked in your trunk or take them with you so as not to attract thieves, just as you would in any other big city.
Chicago has a bad reputation for crime and being dangerous and has consistently been ranked in the top 1-3 spots for most dangerous cities in the U.S. That being said, we’ve been to Chicago more than a dozen times in the past 5 years and have never had any issues. People in Chicago are very kind and look out for one another, unlike anywhere else I’ve ever seen. As with any large city, don’t flash valuables, don’t walk into sketchy-looking places alone at night, and trust your instincts – if something doesn’t feel right, don’t be afraid to get yourself out of the situation or call for help.
If you ever have any issues, duck into an open shop or restaurant and ask for help; you won’t be ignored. Be alert, and be cautious, but don’t let it ruin your trip. We’ve found ourselves in some “sketchy looking” places in Chicago and were completely fine, so be sure to enjoy your time here and if you’re still worried, stick to touristy areas and the main roads during the day and into the evening, and you will be fine.
When to Visit
I personally prefer to visit in spring, summer, or fall when it’s warmer and more activities and events are happening, but it’s awesome all year-’round, and there’s always so much to do no matter the weather.
When the Weather Isn’t Great
Duck indoors, shop, hit up any of the amazing museums in the area, hunker down in a cafe or take your camera and umbrella out and get some great shots of the moody weather and the city’s skyline.
What would you add to this guide? Did I leave anything out? Feel free to ask me questions, leave advice, or share your favorite memory in Chicago below in the comments!
Until Next Time!
Follow Me for More: @AnnieFairfax