Chicago on the cheap: Our experts share their tips

Winging to the Windy City

When Frontier Airlines added service between the Twin Cities and Chicago, they briefly tantalized us with $29 fares each way. Seats that cheap are gone. But you can still find fares so low that they beat the price of gas plus parking at a Chicago hotel, a notoriously budget-breaking expense. Case in point: Earlier this week, a round-trip flight on Spirit, Feb. 17-20, was going for $68. (For no additional fee, you can board with a personal item such as a large purse, presumably stuffed with clean underwear and toiletries. Carry-ons cost an additional $35 one-way; the first checked bag, $21.) A Frontier round trip, April 16-20, came in at $98. Check a calendar, and you'll see the dates I used fall midweek or Saturdays. An itinerary with a Friday departure and Sunday return can cost twice as much. But Wednesday through Saturday makes a nice getaway — especially when it leaves money for more fun.
- Kerri Westenberg, Travel editor

Cheap sleeps

Chicago is a city where I've always had great luck booking last-minute rooms via either Hotwire.com or the Hotel Tonight app. When I decided to go see a Replacements concert at the Riviera on a few days' notice last April, Hotwire gave me a totally decent if not luxurious room for $64/night plus tax at the Inn of Chicago, right in the heart of the Magnificent Mile area. And a road trip to RiotFest the previous year got us the Holiday Inn Mart Plaza in the Loop for $70. Hotel Tonight usually offers some of the nicer, boutique-y hotels at good (if not as great) savings. Of course, parking at these places can really up the cost — $45/day at that Holiday Inn! — but with airfare so cheap now, far fewer Minnesotans will be taking their cars.
- Chris Riemenschneider, music critic

Great lunch, great price

Shopping N. Michigan Avenue, and don't want to spring for RL Restaurant or NoMi Kitchen? Consider a stand-up lunch at tiny Wow Bao (835 N. Michigan; 1-312-642-5888; wowbao.com) in Water Tower Place, where the rice bowls, dumplings and steamed buns known as bao (get the sweet-hot Thai curry chicken version) are priced in the fast-food mode but taste so much better. The house-made ginger ale sports an impressive kick. For power shoppers working up an a.m. appetite (doors open at 10 a.m. Monday through Saturday), there's breakfast bao, too.
- Rick Nelson, food critic

Musical hangouts

Chicago is renowned for such legendary live-music venues as Metro, the Empty Bottle and the Double Door. One spot that only the locals know about is the Hideout, tucked away in an industrial area by the river. Allegedly a Prohibition-era gangster hang, the Hideout looks from the outside like an ordinary house with a big patio. Inside is a classic neighborhood dive bar, and beyond that, a 200-capacity venue starring Chicago music fixtures nightly (cover is usually $5-$10). Honky-tonk singer Robbie Fulks holds down Monday nights, and the long-running, female-fronted alt-country group Freakwater plays March 18 (cab or Uber recommended; 1354 W. Wabansia Av.; hideoutchicago.com).
- Simon Peter Groebner, features editor

Culture on foot

Major art museums in many cities have free days or evenings. But not Chicago, where freebies are limited to Illinois residents at the Art Institute of Chicago (Thursdays, 5 to 8 p.m. year-round; all day Jan. 4-Feb. 11) and the Museum of Contemporary Art (Tuesdays). So out-of-staters can either pay full tab ($25 at the AIC; $12 MOCA) or go for architecture and parks instead. Start at Millennium Park (Michigan Avenue between E. Randolph and E. Monroe), where grand modern sculpture adjoins a charming outdoor ice rink and adjacent cafe. Then cross Michigan Avenue to the Chicago Cultural Center (78 E. Washington St.; 1-312-744-3316; cityofchicago.org), where free concerts, film screenings and performances are staged regularly under the world's largest Tiffany dome, a 38-foot-diameter extravaganza of shimmering peacock blue, green and gold glass crowning a white marble rotunda decorated with mother-of-pearl mosaics and gilded quotations from classical literature. A few blocks south, the Harold Washington Library, honoring the city's first black mayor, is a jaw-dropping 1991 postmodernist masterpiece in carnelian granite and rose brick topped with a blue roof and huge copper-green gargoyles, bundles of grain and medallions depicting Greek goddesses. Inside, check out free exhibits on Chicago history and architecture. And don't miss the trees flourishing in the beautiful ninth-floor winter garden.
- Mary Abbe, art critic

Prices that entertain

Chicago is as famous for deep-dish pizza as it is for its gutsy theater, including improv comedy at Second City, wrenching work at places like the Goodman, Steppenwolf and Victory Gardens as well as Broadway tryouts. You usually can find affordable tickets to shows, but supply is limited. When I checked in late January, Hot Tix (hottix.org) had half-price seats for the Tony-winning "Beautiful: The Carole King Musical," which originated in the Windy City. Half-price seats were also available for shows at some of Chicago's most prestigious playhouses, including "Another Word for Beauty" at the Goodman ($20-$30), "Satchmo at the Waldorf" at the Court Theatre ($24-$29) and stand-up comedy and revues at Second City ($13). Congo Square Theatre, a favorite company of August Wilson's, is presenting Pearl Cleage's "What I Learned in Paris." That well-reviewed show is worth a full-price ticket.
- Rohan Preston, theater critic