Chicago ain’t cheap. As the “Capital of the Midwest,” it’s noticeably less expensive than New York and Los Angeles. But as the third largest city in America, Chi-Town is still noticeably more expensive than the national average.
But you won’t find a cleaner, nicer, and taller big city than Chicago, which makes it totally worth seeing at least once in your life. Here are a few of our favorite tips to affordably visit the Windy City, without compromising on its awesomeness.
Where to Stay
If money isn’t an issue, opt for the breathtaking Peninsula or Langham hotels, both of which retail for over $1000 a night and are considered two of the swankiest hotels in the entire country. But if you’re looking to experience the best of Chicago for less, we’ve rounded up three more affordable hotels that don’t compromise on coolness.
Virgin Hotel—Located in the Chicago Loop just steps from Millennium Park, the Virgin Hotel is an uncannily chic pick and phenomenal value for what you get: sleek rooms, rainfall showerheads, rooftop bar, and live DJs in the heart of the city’s skyscrapers.
CitizenM Downtown—Although more compact than Virgin, the playful and artful CitizenM Downtown is just as delightful and perfectly situated. Better yet, average nightly rates can often be found for sub $150—soundproof windows, blackout blinds, and killer views very much included.
Moxy Downtown—No matter where you’re headed, there’s a 99% chance you’ll have fun staying at any Moxy hotel, especially the buzzy one in Chicago’s River North Neighborhood. At the Moxy Downtown, you’ll find contemporary lighting, floor-to-ceiling windows, and free parking. If you’re traveling with a fuzzy friend, pets 40 lb. and under are welcome for an additional fee.
The Bean in Millennium Park
Photo by Ravi Patel on Unsplash
What to Do
There’s plenty to see and do in Chicago without breaking the bank, with an abundance of free museum days, free sightseeing tours, and even discounted food options.
To get the lay of the land or learn more about the city, start with a free greeter tour led by a local volunteer. It’s a great way to orient yourself and take in the clean, wide, and flower-filled streets that the city is known for. Next, instead of a $50 boat tour of Chicago’s architectural marvels (which is awesome by the way), you can get equally close to them with a $10 day-pass on water taxis, or stroll the Riverwalk on foot.
Other highlights include Millennium Park and its reflective “Bean,” the classic Buckingham Fountain of Married, With Children fame, the Magnificent Mile, and free museum days for Illinois residents. While you’re in town, don’t miss Art Institute of Chicago, which many critics, visitors, and yours truly consider the greatest art museum in America.
To get high for less, head for the 360 Chicago Observation Deck, which is $15 cheaper than Skydeck Chicago. And don’t sleep on the Lakefront Trail, Navy Pier, the city’s sprawling, ocean-like beaches, and Green City Market for some inspiring vibes, amazing views of the lake and skyline, plus inexpensive pizza, pickles, and pastas.
Speaking of food, don’t miss Portillo’s for some of Chicago’s greatest street eats, Giordano’s for the best deep-dish pizza (Don’t @ me, Lou Malnati!), and Falafel & Grill for fantastic Middle Eastern plates.
Chicago winters are no joke, but there are bargains to be had.
Photo by Alex Azabache on Unsplash
Bonus Tips
If you don’t want to pay higher prices for everything, including flights, hotels, and activities, avoid visiting Chicago in summer. For the cheapest, albeit hella cold option, visit in winter, which is still a lot of fun. For the best of both worlds, consider the shoulder seasons of spring and fall.
A few other ways to save: fly into Midway instead of O’Hare. Both are basically the same distance from downtown, but the former usually caters to budget airlines and regional flights. You can save up to 50% on full-price admissions to cultural destinations like the Art Institute and Field Museum with the Chicago CityPASS. Skip the Ubers and hop on the easy to navigate L (aka “elevated”) trains, especially from the airport.
Lastly, White Sox games are much cheaper than seeing the Cubbies. (Better food, too.) Either way, you can definitely live large when visiting Chicago. You just have to know where to look.
