5 Go-To Places To Take Friends When They Visit Chicago (That Won't Break The Bank)

"You wake up in Chicago, pull back the curtain, and you KNOW where you are. You could be nowhere else," Anthony Bourdain said of his Windy City experience in an episode of "Parts Unknown" — and that's exactly how I feel whenever I come home. I grew up just outside the city, spending countless day trips, field trips, weekends, and summers in Chicago, then living there for various stints as an adult. Thanks to my large family and many friends who still live there, I've always had a foot firmly planted in the "metropolis, completely non-neurotic, ever-moving, big-hearted but cold-blooded machine with millions of moving parts," as Bourdain put it. I still call Chicago home, and that grounded history — combined with returning regularly with fresh eyes — makes me uniquely qualified to play part-time tour guide.

Deciding what to do in Chicago means narrowing it down. Each neighborhood has its own personality and pull. "If we're in Lincoln Park for dumplings, we can hit the ZooLights, and that bakery with the ube cake is nearby..." the conversations go. Some of it is seasonal: Summer brings festivals, concerts, and lake days, while the holidays transform the city into a winter wonderland. We usually mix in thrifting, a museum or architecture tour, a show or comedy set, something outdoors — and always good food. Having current city residents helps me avoid Chicago's tourist traps and lean into the city's funny, smart, down-to-earth vibe.

This list reflects what I actually do in Chicago year-round — indoor and outdoor activities that showcase the city's best without draining anyone's wallet. I've drawn from decades of personal experience, cross-checked with reviews and Reddit to round it out. And if your budget is truly zero, Chicago offers no shortage of free, iconic activities worth building a vacation around.

Thrifting in Chicago is like wandering through interactive museums full of history and relics — you don't even have to buy anything, and that's why I love it. No matter which part of town you're in, you're likely to find vintage or thrift shops around the corner. One favorite is Brown Elephant. Located in Andersonville, a neighborhood that blends Swedish roots with one-of-a-kind stores and unmatched food, it's a multiroom consignment shop with furniture, clothing (including designer), home goods, vintage items, and art; plus, proceeds go toward supporting LGBTQ+ healthcare at Howard Brown Health. "'Find' is the operative word," wrote a Yelp reviewer. "But discovering something cool for the price of a couple of Taco Bell burritos is its own reward." Hit Rattleback Records afterward, just across the street, to peruse used and new vinyl.

Village Discount Outlet is a true basement-style thrift store with several locations, perfect if you love hunting for hidden bargain gems. "Cheap thrift, but you've got to dive for it," wrote a Redditor. Over in Edgewater, Broadway Antique Market is truly like a museum, with two levels of curated vintage everything, from mid-century furniture to historic collectibles, though a little less bargain-friendly than some others. "This place is the king of mid-century finds. Truly a gem in Chicago," wrote a Tripadvisor reviewer.

Consignment and specialty vintage shops abound throughout Chicago, whether you're on the hunt for everyday wardrobe, period-specific clothing, or designer art. I also love Woolly Mammoth, a shop full of antiques and oddities, Wicker Park's Vintage Underground for Art Deco jewelry, and Monarch Thrift, a cute, woman-owned consignment in Logan Square.

"Lack of a sense of humor will not get you far in Chicago," Anthony Bourdain once wrote — which may be why the city has quietly produced some of the country's most notable comedians. From Bill Murray and John Belushi to Tina Fey and Amy Poehler to Keegan-Michael Key and Jordan Peele (Key and Peele), many big names cut their teeth here, largely thanks to Chicago's improv-forward DNA and institutions like The Second City, which put the city on the comedic map. Venues like Annoyance Theatre, the Lincoln Lodge, and iO feel almost like neighborhood hangouts, with rotating shows and performers who are happy to let you buy them a beer and say hi after the show. The Comedy Clubhouse is a highly rated theater and "perfect way to spend Saturday night in this intimate and cozy theatre," as a Yelp reviewer put it, while Logan Square Improv offers $5 shows Wednesday through Sunday. "The crowds are fun, the hosts bring high energy, and the shows are fantastic," wrote a Yelp reviewer. "Logan Square Improv's $5 shows are a great use of your money," agreed another. 

One of my favorite long-running iO shows, "Improvised Shakespeare," is reliably hilarious, and their lobby bar is a fun place to hob-nob with the comics themselves. Tickets are usually about $35, but many iO shows cost less. For stand-up, classic Chicago scenes Zanies or The Den deliver, or you can brave Chicago's underground scene — Chicago Open Mics lists low-stakes spots where you might find something weird... or maybe even brilliant.

If live comedy isn't your jam, I also love the Music Box Theatre — a historic, two-screen cinema that has become an indie-cult-international-classic film darling, known for fun, themed screenings and retrospectives. Or, check out well-executed live performances at Chopin Theatre.

One of the first things I do when planning a trip home is check whether my trip dates overlap with any free museum days. Chicago has some of the best museums in the country, from the world-renowned Art Institute to the Field Museum of Natural History to the DuSable Black History Museum and Education Center. Free museum days — which Choose Chicago has tracked for convenience — can really help keep costs low, but many museums charge reasonable prices any time of the week. The National Puerto Rican Museum in Humboldt Park, the National Museum of Mexican Art in Pilsen, and the stunning Chicago Cultural Center with its stunning stained-glass domes are always free and highly recommended — I love revisiting as a local and taking new friends. Mindworks, a free behavioral science museum across from the Art Institute, has interactive exhibits and inclusive studies. "This is a very interesting place," wrote a Tripadvisor reviewer. "Tiny, but with enough thought-provoking displays and activities to make it well worth your while."

One underrated gem is the Garfield Park Conservatory, which is free for local residents and charges a small fee for non-residents. (When I texted my sisters to see what would be top of their list to do last time I came to town, they both listed this first, as did one of my city-dwelling friends who got engaged here). From the Fern Room to the Desert House to the outdoor gardens, you'll feel oxygenated and relaxed after a morning spent in the conservatory. It totally counts as "touching grass!" "Filled with an incredible variety of plants and beautifully designed rooms that make you feel like you've stepped into a completely different world," wrote a Tripadvisor reviewer.

Chicago's a culinary melting pot, and cultural enclaves can provide some of the deepest flavor for affordable prices. Devon Avenue, or Little India, is dedicated to the culture and flavors of South Asia. Tandoor and masala wafts from eateries as shoppers get fitted for saris and sherwanis in the many garment stores. Sip pink Kashmiri chai for under $4 at King Sweets, then taste flavorful chicken tikka at Curry Kitchen or fluffy biryani at Bundoo Khan – both cost less than $20.

We love Chinatown on the South Side (go Sox). You'll know you've arrived by the Chinatown Gate, with the Nine Dragon Wall just beyond. Order family-style Cantonese at Triple Crown or MingHin Cuisine and juicy handmade dumplings at Qing Xian Yuan before snapping selfies with the Chinese Zodiac animals, then grab boba at Saint's Alp before browsing the shops. On the North Side (go Cubs), Argyle Street — affectionately nicknamed "Asia on Argyle" or "Little Vietnam" — offers another glimpse of the city's Asian diaspora. Order pho and egg rolls from Nhà Hàng, a banh mi from Nhu Lan Bakery, or dim sum at old-school Furama. In both neighborhoods, you'll also find cultural celebrations from the Lunar New Year to the Mid-Autumn Festival.

Years ago, my sister and I scouted meals featured in "The Bear" — thick chocolate cake from Loaf Lounge, slices and cocktails at Pizza Lobo, and drool-worthy breakfast sandwiches from Filipino hotspot Kasama (pro tip: order ahead to-go, or prepare to wait!). Today, pricey food tours cater to the show, but you don't need to spend big bucks to walk where Carmy did — just go eat! You can also try Anthony Bourdain's favorite Chicago restaurants or find the best hot dogs in the city – there's something for everyone.

Chicago weather can be unpredictable and extreme, but locals take advantage of every good-weather window and bundle up when there isn't one. The Chicago Riverwalk has transformed a once-industrial area into one of the city's best outdoor pedestrian spaces, free to stroll with striking views of architecture, public art, and seasonal lighting projections on the storied Art Deco Merchandise Mart building. Upriver, Chicago's Wild Mile, the world's first floating eco-park, offers a peaceful boardwalk and kayak launch while restoring native wildlife and filtering pollution. Paddle with Urban Kayak, or hop on a Chicago Water Taxi for a $10 DIY cruise, the locals' version of a more expensive boat tour.

Chicago's beaches are summertime social hubs. I love North Avenue Beach for its buzzy, beachy energy; Oak Street Beach for excellent skyline views; and Montrose Beach, where we can bring my friends' dogs — even in winter. The Lakefront Trail runs for miles along Lake Michigan, connecting beaches, parks, and neighborhoods, including free-to-visit Montrose Bird Sanctuary in Lincoln Park, home to the famed "Magic Hedge," where tens of thousands of migrating birds gather to rest en route. For $18 per day, renting a Divvy bike is a great way for visitors to explore, including the elevated 606 Trail, a long park, and perhaps a better version of the NYC Highline. Seasonal neighborhood pop-ups like Green City Market and festivals like Taste of Chicago make the city feel like a block party all summer long.

Millennium Park in the heart of downtown is a tourist go-to, but locals will agree to go for the free concerts all summer, and come wintertime, a skating rink pops up in front of Cloud Gate "The Bean," where you can take advantage of free admission if you bring your own skates, with rental fees available onsite.

There are so many places I'd want to take you if you called me up and said you were coming to Chicago. It was tough to narrow it down — should the list feature five singular activities or places? Or five neighborhoods packed with destination-worthy spots within a small radius? In the end, I pulled from the general categories I typically cover when friends and family and I are enjoying the city — the kinds of places I actually return to, not just the ones that show up on every "Top 10 Chicago" list. That way, whether you're a Chicago first-timer or a repeat visitor, there's a variety of options to help you find less tourist-saturated, budget-friendly destinations. 

In addition to my own personal experience navigating the city as a part-time resident, I drew on Reddit, Tripadvisor, Yelp, and Choose Chicago, a city tourism site — not to chase hype, but to confirm hours, prices, and accessibility, and help narrow down the million things you could possibly do in the city.

"Breaking the bank" means different things to different people, but I tried to keep everything within what most working folks would consider a reasonable range — prioritizing free attractions, low-cost experiences, budget-friendly eateries, and places where you can control how much you spend. Some things are totally free; others cost a bit, but none require luxury-level splurging. Ultimately, Chicago is a working person's city. Though it may have been nicknamed for its blustery politicians, it remains a friendly, unpretentious Midwestern city that welcomes tourists and residents alike to partake in the best life has to offer, no matter how deep their pockets are.