My husband Robin and I had such an awesome weekend in Chicago! I was traveling with a friend for Spring Awakening music festival, and Robin was in town for work and was able to join us for some of our adventures! I finally got to see Tiësto live (and right up against the barrier) after being a fan of his for more than a decade, as well as some other awesome DJs like Steve Aoki and Tritonal, so that alone made it a great weekend. We were also able to finally take time to really explore the city and get to know all of the awesome things it has to offer. Typically when we visit Chicago, we are there no more than a night or two, typically to fly out of O’Hare airport, but spending 4 consecutive days here was such a great way to spend a long weekend! You can check out my friend’s awesome guide to Chicago as a single, female traveler here!
Where to Stay:
We stayed at the stunning Radisson Blu Aqua Chicago, which has won numerous awards for its unique architectural design, fantastic staff, and unique decor, and it was one of the coolest hotel experiences I’ve ever had! The view of Millennium Park and the rest of the city from our 11th floor Park Suite was phenomenal and allowed us to see so much of the city and lake, sometimes we’d sit up late in our living room, watching the city from above while planning out our next day’s adventure, before heading to sleep in the massive, plush king size bed. The floor to ceiling windows, gorgeous, open floor plans, and unique art from the city made the room feel even more luxurious. The Radisson Blu Aqua Chicago had some of the best hotel staff I’ve ever encountered (and I spend about 1/2 of the year traveling!), who went out of their way to make us comfortable, ensure that we were happy with every aspect of our stay, and did it all with a genuine smile on our faces. We felt right at home and everything we encountered from the room amenities to the valet were designed to make guests feel welcome, comfortable and simplify their stay. If you’re ever in the area, I highly recommend staying here and enjoying the atmosphere, the food, and the rooftop pool! Check out my guide to the hotel here.
Where to Eat:
The Hampton Social 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 omelette with a gluten free berry pancake and it was incredible! Robin ordered an eggs Benedict topped with spinach and angel hair pasta, which looked as strange as it sounds but came highly recommended by the restaurant staff and the people sitting next to us. While it wasn’t his favorite, he did help me finish my meal and agreed that the omelette and pancake were some of the best he’s ever had! This place was right around the corner from the Radisson which made it convenient, however 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.
Giordonos is my favorite pizza place in all of Chicago for incredible, Chicago-style deep dish pizza, and they even have gluten-free options too! Plan to wait 45 minutes-an hour for a deep dish pizza to cook, or call ahead and pick it up!
Sweetgreen Salads 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 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 just have to go explore it for yourself, you won’t regret it.
Shanghai Terrace 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 a beautiful, exotic location somewhere in China, the staff were cheerful and kind, and the menu had something for absolutely everyone.
The Violet Hour has a hidden entrance covered by a changing mural and a single bulb, making it difficult, yet rewarding to find. 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.
Filini Bar & Restaurant inside Radisson Blu Aqua Hotel are great places to have dinner or grab a drink, and they offer indoor or outdoor seating.
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, which is 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, The Field Museum, Museum of Science and Industry or the 360 Chicago Observation Deck, and the Skydeck Chicago. For the 2 “or” options, with CityPASS if you want to see all four attractions, you get even further discounts when buying additional tickets, which means you don’t have to miss out on anything! Skipping lines, saving money, seeing more of the city, what’s not to love? Explore my CityPASS experience in Toronto, ON here and here, and check out which other cities offer CityPASS’ convenience 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 so many tours from architecture or food and drink tours to more sordid and supernatural tours. If you’re looking for something more adventurous, there are two very large, public rock climbing walls in Maggie Daley Park, you can go skydiving over Lake Michigan with Skydive Midwest. You can also find places to rent paddle boards, 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 and 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 gorgeous 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.
Navy Pier is definitely a can’t miss area of Chicago. This is where the Insta-famous 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. The activities and events happening on the pier change daily and weekly, so be sure to check out the schedule of events here prior to your trip to best plan your time here.
Millennium Park, home of the famous, mirrored “Bean“, always has something going on. While we were in town, there was a Jazz Festival and wine tasting event happening.
We were in town for Spring Awakening, which is one of many concerts that was happening 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 to, 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 a number of clubs, bars, pubs, shows, and things that are open late. 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 once we arrived we parked our car with the valet and hiked around town on foot. 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, which are cheaper than taxis and tell you the total fare beforehand. There is also a subway system and an above ground train called the “L” which can get you wherever you need to go.
Parking in Chicago can be a pain, but it doesn’t have to be. We parked our car with the valet at the Radisson and didn’t have to worry about it being accidentally damaged (street parking can be scary!), and took 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. 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.
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 just 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 there are more activities and events 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!
Explore the World with Me:
Complete Traveler’s Guides: Baden-Baden, Germany | Beverly Hills | Carmel, IN | Chicago| Colmar, France | Grand Rapids, MI | Greenland | Heidelberg, Germany | New Orleans | New York City | Niagara Falls | Querétaro | Toronto| Traverse City, MI | Tucson | Tulum | Vatican City | Venice |
Luxury Hotels of the World: Amway Grand Plaza: Grand Rapids | Casa de la Marquesa: Querétaro | Der Kleine Prinz: Baden-Baden | Grand Hotel: Mackinac Island | Hotel Monteleon: New Orleans | Radisson Blu Aqua: Chicago | SchlossHotel HugenPoet: Essen | Titanic Chaussee: Berlin | Townsend Hotel: Birmingham| Weber’s Boutique Hotel: Ann Arbor | Zamna: Tulum |
Luxury Restaurants of the World: Barrel Back: Walloon Lake | Hinoki & the Bird: LA | Kin Toh Treehouse in the Jungle: Tulum | Kitchen Table: Tulum | Ladurée Paris | Matcha Mama: Tulum | Prost Wine Bar & Charcuterie | The Real Coconut:Tulum | Rosa Negra: Tulum | Sushi Grand: Mackinac Island | What to eat Grand Hotel Mackinac Island | 10 Best Places to Grab a Drink on Mackinac Island | 15 Best Places to Eat in Grand Rapids | 20 Best Places to Eat in Tulum | 50 Best Places to Eat in Michigan |