How to Spend Two Fancy but Affordable Days in Chicago
Eat like a Top Chef, sweat with a sauna master, access rare art, and more tips to living large without going broke in the Windy City
Chicago is a blue-collar city built by dreamers willing to roll up their sleeves and make magic happen (ahem, Michael Jordan, Oprah Winfrey, Michelle Obama…). But despite its reputation for working class roots, Chicago—with its sparkling skyline, iconic skyscrapers, and gothic architecture, all sitting on a lake dotted with boats—belies some serious luxury. It’s easy to have it all here—if you know where to look.
Like all big, desirable cities, of course Chicago can be pricey, but the city’s size also offers plenty of opportunities to offset spending through free cultural events and quick-service prices for high-end meals. Getting the upgraded version of Chicago is not an impossible task—on any budget.
Whether you’ve spent your whole life in Chicago and are looking to see a different side of the city or are visiting for the first time on a treat-yourself trip, here’s the elevated, ever-so-slightly fancy guide to 48 hours in the Second City.
Who I am: I’m Ximena, a freelance writer based in Chicago. I’ve spent more than three decades in the city, exploring every corner of it via the CTA. I love the wide spectrum of what you can do, eat, and see here. When not on a food adventure, you’ll find me at the Alamo Drafthouse in Wrigleyville, a Sky basketball game, or any of the free arts and cultures events happening multiple times a week.
Before you go
Know the seasons. Nothing beats summertime in Chicago. The days are long and perfect for patio dining, sailing during the sunset, and walking/biking/running along the lakefront. This also means that July through September is peak tourist season. Crowds begin to thin at the start of fall as the days start to shorten and temps begin to drop (providing the ideal atmosphere for those with low heat tolerance). The weather is the most unpredictable during the spring season (late March through early June), when it could rain, snow, and be over 80 degrees—all in one day. The winters are brutal, but the city makes up for it with a jam-packed schedule of Bulls, Bears, and Hawks games, opera season, and plenty of ice skating for those who don’t mind the chill.
Be prepared for crowds. If you’re dining anywhere without a reservation and want to sit outside, expect long waits for a table during patio season. During the warmer months, there’s also heavy traffic on Lake Shore Drive and street closures during Cubs games, Sueños, Lollapalooza, and NASCAR Street Race. Public transit and scooters are often the best ways to get around.
Use public transit. The CTA, or “El” as it's known colloquially, might have a bad rap with locals because of delays, but it’s still one of the most efficient ways to get across the city. A $5 daypass gets you unlimited rides on all the train and bus lines. If you’re not in a rush, choose the Brown Line when you can. The views crossing the river between Merchandise Mart and Washington/Wells are spectacular and worth the potentially long wait for a train.
Where to Stay
Hotel Zachary
Wrigleyville, the neighborhood surrounding the stadium where the Chicago Cubs play, has turned into a travel destination for baseball and country fans. The boutique Hotel Zachary is close to the action and the best place to stay if you love crowds of sports fans and street festivals. The hotel’s Alma bar offers a peaceful post from which to watch all the activity. It’s also the only hotel within a half mile of the stadium.
The Hoxton
Located in the West Loop, Chicago’s trendiest neighborhood, the hotel is known for its swanky design (think lush velvets, rich browns, and brass finishes), spectacular view from the rooftop (where you’ll find Cabra Cevicheria, the Peruvian-inspired restaurant by chef Stephanie Izard), and a hidden basement bar that even locals love to frequent. The rooftop pool is only for guests, and comes in handy during the hot summer months.
The Langham
In a city with plenty of high-quality options, The Langham is the best choice if you’re planning to actually splurge. Perched on the Chicago River, in the heart of the city, the luxury hotel has stunning views that are hard to beat. The onsite Chuan spa offers an array of wellness treatments rooted in traditional Chinese medicine , while the onsite restaurant, Travelle, serves upscale American classics and drinks that are meals in themselves—a vodka martini is served with two oysters, caviar, and Thai chili oil.
Two Slightly Fancy Days in Chicago
Day 1
Morning: Fuel up with Michelin-starred dishes at a discount and then get treated to a head spa
- A dinner reservation at Kasama, the world’s first Michelin-starred Filipino restaurant and James Beard Foundation award winner, is one of the city’s hardest to obtain. Fret not: Frequent diners know the restaurant’s breakfast dishes and pastries are just as delicious as the evening menu and come at a fraction of the cost. With one-of-a-kind options like the ube and huckleberry basque cake, coconut black sesame black macaroon, and longanisa breakfast sandwich, you can expect long lines, but you can beat the crowd (and the possibility of sold-out items) by ordering online.
- Make your way over to Lincoln Park where H20 House has turned one of the best parts of getting a haircut (the scalp massage during the shampooing) into a relaxing 60-minute treatment for your head. The spa service even includes a quick blow-dry before you hit the town.
Midday: Find the cool kid’s art museum then devour classic Chicago dishes
- Everyone knows to go to the Art Institute of Chicago to see the largest collection of Impressionist and Post-Impressionist art outside of the Louvre. But Wrightwood 659 is where the IYKYK crowd is headed. The mansion-turned-museum designed by world-famous architect Tadao And features provocative, curated exhibitions from notable artists such as Ai Weiwei, Michiko Itatani, and Rirkrit Tiravanija (this is the city’s ritziest neighborhood after all). Take a stroll through the streets bordered by Wrightwood, Lakeview, Fullerton, and Orchard for a glimpse of historic architecture nestled among modern design and lavish landscaping. Of particular note is the Wrigley Manson with its intricate baroque terra cotta exterior; the Morningstar Mansion which sprawls across eight lots, and the 500-600 blocks of Deming Street where the city’s wealthiest entrepreneurs rebuilt their homes after the Great Chicago Fire of 1871 .
- By now you might have worked up an appetite, so walk down to Clark Street for your pick of iconic eats. No visit to Chicago is complete without a stop at the infamous Wiener’s Circle. Sure, at this hour you’re not going to be berated by the foul-mouthed staff, but the hot dogs still taste the same in the daylight. Order a Chicago dog (charred, not steamed) with everything on it. Prefer something other than sausages? Del Seoul’s sesame-chili shrimp tacos; Lito’s chorizo, cheese, and potato-stuffed empanadas; and Aloha Eats’ chicken katsu with spicy curry gravy are just steps away. For dessert, grab a sweet treat from Cupcake Wars alum Molly’s Cupcakes, known for its gooey center cupcakes such as the peach cobbler.
Take this home
J.P. Graziano’s Beef Kit
Chicago is a food town. For the last 10 years it’s hosted the James Beard Foundation Awards while FX’s Emmy-nominated series The Bear has continued to draw attention to the dining scene—particularly the Italian Beef sandwich. Take a taste of Chicago home with you via J.P. Graziano’s beef kit. The family-owned sandwich shop has been in business since 1937 and is a staple of the city.
Afternoon: Then go shopping
- Next, head to North Center for a shopping spree of makers prioritizing high-quality, ethical consumption versus fast fashion. At Production Mode, the slow fashion boutique invites customers to be a part of the design process. The shop, owned by former labor rights organizer Jaime Hayes, offers complimentary made-to-measure services for their in-house collection of women’s ready-to-wear and formal attire and also carries indie brands that can be tailored for an additional cost. The store is located on a block full of cute shops including Soutache, a buttons and ribbon specialty shop (many are vintage and collectible, and Maili, the owner, will replace buttons at a reasonable price); Bari Zaki, a paradise of all things paper; and Knit 1, a yarn haven of natural fiber knitting and crocheting supplies.
Evening: Enjoy the sunset on the Riverwalk and end the night Chicago-style
- Soak in the city’s architecture with a stroll along the Riverwalk. There’s a number of small parks, lookout points, art installations, shops, and bathrooms along the 1.25-mile route. After all that free fun, you’ve saved up enough for a meal at Indienne, the city’s only Indian fine-dining restaurant (which also boasts a Michelin star). The dreamy space is filled with warm pinks and greens and everyone seems to have gotten the memo to dress up, weeknight or not. Chef Sujan Sarkar’s dishes, such as the pani puri, avocado kabab, and morel samosa, are all as exciting to look at as they are to eat. If that’s not your jam, other nearby hotspots include Beity, the city’s first and only Lebanese tasting menu, and Esme, an eatery with a high-art concept.
- Close your night at The Drifter. The matchbook-sized speakeasy is located in the back basement of The Green Door Tavern and has been around since Prohibition. For the cost of a drink and an $8 cover, visitors are treated to a rotating mix of magicians, cabaret singers, and burlesque dancers perform in this 45-seat venue that feels as if you’ve stumbled on a socialite’s private shindig. A cocktail menu with more than 100 options rotate nightly. (Only 15 are available each night and selected via a tarot deck.)
Day 2
Morning: Start with a sweat
- Begin your day with 75 minutes of self-care during a visit to Eastend for a sauna session led by the city’s only saunamaster. The just-opened facility is the only place in the city offering sauna-specific classes.
Midday: Get cultured then stop for sushi
- There’s nothing fancier (or sexier) than smarts, and a visit to the Newberry Library offers a peek into a treasure trove of historical artifacts and knowledge. Among its collection is Popol Vuh, the earliest surviving copy of the Mayan creation story; handwritten scores by Mozart, Chopin, Mahler, and Wagner; and more than 700 American Revolutionary pamphlets. “Native Pop! How Indigenous people have shaped popular culture” is among the current exhibitions.
- Grab lunch from 312 Fish Market in Chinatown. The modest sushi spot, located in a food court, is a surprising favorite for raw fish aficionados, including Top Chef winner Joe Flamm.
Afternoon: Take in the city’s architecture
- One of the best ways to see the city (especially if you’re short on time) is from a bird’s eye view. Channel your inner billionaire (for a scant $TK an hour) with a helicopter tour, that allows you to take in the sights without the traffic. Fly Heli offers a 16-mile loop around the city’s most scenic landmarks (including the Bean, Millennium and Grant Park, and Navy Pier).
- Scared of heights? See the city by water. The Four Seasons Hotel Chicago offers a private yacht charter that can accommodate up to 12 people and includes food, beverage, and staff. The Chicago Boat Company offers more affordable (year-round) options for people who want to party on the river, while the Chicago Architecture Center’s River Cruise tour is a favorite among design enthusiasts and history buffs.
Evening: Spend a night out in the park then dance till dawn (or last call)
- Chicago’s Department of Cultural Affairs and Special Events offers a plethora of free activities across the city’s parks. Among the options are live theatre by the award-winning Chicago Shakespeare Theatre; fan favorite films like Top Gun: Maverick, Grease, and Coco; and concerts from international artists such as Bomba Estereo. Check the calendar to see what’s scheduled during your visit.
- Call it quits with a scooter ride back to your hotel or pop into Blind Barber, a modern speakeasy turned mini club, for a nightcap that can quickly turn into an all-night dance party with the city’s tastemakers.
If you have three days
All the above, but add…
- Skip the $30+ admission fee to the Sears Tower and John Hancock Building and put those funds towards your meal with a view instead. La Merenda Toscana, Italian happy hour, comes stateside courtesy of the St. Regis Chicago. Available on Saturdays and Sundays from 2 to3:30 p.m. at Tre Dita, one of the city’s most popular restaurants, guests soak in spectacular lake and riverviews while enjoying a tkadjective snack course. Sixty bucks includes bites like cacio e pepe gougeres, smoked trout mousse with trout roe, and pappardelle fritti, as well as a selection of housemadesweets.
- Make your way down to Wintrust Arena (or if you’re lucky, the United Center) for a Sky game. In a town Michael Jordan built, the Sky are the latest pro team to bring the city a championship title.
- With more than 10 acres of green space, the Garfield Park Conservatory is one of the largest and most beautiful conservatories in the world. Spend a few hours (or a whole day) roaming the space that feels as if you’ve been transported to Jurassic Park (minus the scary dinosaurs). It’s free for city residents and $10 for adults.
If you have four days, plus
All of the above, but add...
- There’s no shortage of live music to choose from in Chicago, but The Salt Shed’s elevated-but-not-stuffy vibe (plus plenty of local dining and shopping options inside the multi-use space) is the go-to choice for the person who dreads overcrowded venues. The Marias, Nick Cave, Mount Joy, and Mars Volta have all performed in the open-air venue which boasts the Chicago skyline and river as its backdrop. Upgrade your ticket to premium for access to the venue’s balconies with unrestricted views of the city, no-line bathrooms, and indoor/outdoor seating.
- From The Matrix and Home Alone to The Blues Brothers and Ferris Bueller’s Day Off, Chicago has played a significant role in the cinematic universe and cultural zeitgeist. So it only makes sense to experience a film while you’re in the city, and there’s no better place to do that than the Music Box Theatre. For 96 years the movie house has served its community as a meeting ground for movie buffs across the spectrum. With horror movie marathons from across the world, Sound of Music sing-a-longs, and screenings of films thought to be long-lost (like the original Nosferatu), the Music Box is a must-visit for cinephiles.
- Unwind and prepare to return to normal life with a 60-minute soak at Aire Ancient Baths. The tranquil space includes several pools heated at different temperatures in a restored warehouse with soaring ceilings.