Chicago..
FRUGAL TRAVELER
A Cheapskate in Chicago
Recommendations from a city-dweller on where to find excellence in music, art, theater and food without spending a fortune
In Chicago, the Millennium Park sculpture, “Cloud Gate,” by Anish Kapoor, is part of a free Chicago Greeter tour of the downtown Loop area.
Credit...Michelle Litvin for The New York Times. Art by Anish Kapoor Cloud Gate, 2004
By Elaine Glusac
Elaine Glusac spent a week on a tight budget, exploring the city where she has lived for more than 30 years.
July 22, 2024
One June morning, I went to see what the tourists were up to in Chicago, where I live. My mission was to join them while adhering to a strict travel budget. So I started with a free Chicago Greeter tour of the downtown Loop, ground zero for visitors and home to popular attractions like Millennium Park and the Art Institute of Chicago.
Run by Choose Chicago, the city’s tourism marketing organization, the Greeter program pairs visitors with a local volunteer for a guided walk. Our guide, Janice Rosenberg, led me and eight visitors from Spain, Mexico and France on a 90-minute walk around the Loop. She pointed out famous sites like the Millennium Park sculpture by Anish Kapoor, “Cloud Gate,” known as “ The Bean,” and hidden gems like the “ Rushmore” mural, by the painter Kerry James Marshall, devoted to the women who have shaped Chicago. Ms. Rosenberg also identified hallmarks of classic Chicago architecture, including windows designed to catch lake breezes before air-conditioning was universal, and explained to the Europeans that a department store built in 1893 “is old for us.”
It was a dense serving of Chicago history and culture at an unbeatable price (though tips are welcome; I contributed $5).
Big cities, generally, are good places to cheap out as a traveler. Transportation options tend to be affordable. Chicago’s L train, for example, costs $2.50 a ride; day passes are $5.
And Chicago, newly popular with set-jetting fans of the restaurant-focused FX series “The Bear,” anchors the Midwest, a region known for its thrift. There are plenty of things to splurge on — the venerable Lyric Opera of Chicago or Michelin-starred restaurants — but you can experience excellence here in music, art, theater, food and more without digging deep into your pockets.
I spent a recent week living — and scrimping — like a tourist in Chicago. Here are some of my recommendations on how to save.
Motels and rentals
The Ohio House Motel, in Chicago’s River North neighborhood, is one of the city’s budget options, with big, clean rooms.
Credit...Michelle Litvin for The New York Times
What travelers spend on lodging in Chicago depends on when they travel. Average daily hotel rates in 2023 tracked by the commercial real estate analytics firm CoStar Group swung from $114 in chilly January to $197 in balmy June.
Among budget options, the 1960s-vintage Ohio House Motel in River North offered clean, spacious rooms (I paid an average of $127 a night, including breakfast). Those who drive to town will find parking at its surface lot ($29) is cheaper than at many area garages.
Testing another thrifty choice, I booked a night with Sonder, a service that rents furnished apartments online and automates communication, including sending access codes at check-in time (a downtown studio recently started at $129). The only drawback was finding someone to talk to for local advice. Answering an inquiry about where out-of-towners might park their cars, one of its chatbots told me to do a Google search.
Chicago’s homegrown sandwich, the Italian beef — popularized in “ The Bear” — costs $9 at Mr. Beef on Orleans, the inspiration for the series.
Credit...Michelle Litvin for The New York Times
Ms. Rosenberg ended her Chicago Greeter tour at Daley Plaza, which is filled with food trucks every Friday from May to October. She encouraged visitors to enjoy the bargain meals while taking in the 50-foot-tall unnamed Picasso sculpture.
For a more evergreen option, I walked a few blocks to the Loop’s Revival Food Hall and its Danke restaurant for the Secret Sandwich ($11.50), a baguette slicked in savory duck liver mousse and layered in pork belly.
My favorite frugal approach to sampling the culinary diversity in Chicago is to seek it in a sandwich, a takeaway staple deftly adapted across a range of styles, including Vietnamese French dips, Japanese “tamago” egg salad and Mexican tortas.
Chicago’s homegrown sandwich, the Italian beef — popularized in “ The Bear” — costs $9 at Mr. Beef on Orleans, the inspiration for the series.
I asked Mike Gebert, who writes the local dining newsletter Fooditor, for his tips.
“To me, part of the secret is not immediately heading downtown for everything,” Mr. Gebert said. “I look for places in neighborhoods.”
His neighborhood theory meets my sandwich thesis at Kasama in Ukrainian Village (also featured in “The Bear”), where I headed for breakfast the next day. Celebrated for its Filipino tasting menus in the evenings, by day the restaurant serves bakery and diner fare that draws long lines. I avoided them by ordering its breakfast sandwich with longanisa sausage, egg and cheese ($11) online and picked it up to go.
Later that day, I traveled just a bit farther northwest on the Blue Line L to the Logan Square neighborhood for another Chicago original, the jibarito ($8.95) at Jibaritos y Mas. The Puerto Rican invention substitutes fried slices of plantain for bread, bookending grilled chicken, pork or beef for a magnificent mess.
At 8:30 p.m. on Sundays at Simon’s Tavern, free performances draw music lovers. Above, a recent performance by The Country Doctors.
Credit...Michelle Litvin for The New York Times
Off-peak windows rule the bargain entertainment circuit. At 2:30 on a Saturday afternoon, I was too late to score a seat at the Green Mill Cocktail Lounge in the Uptown neighborhood for the weekly 3 p.m. variety show, the Paper Machete. I joined the standing-room-only crowd for the free two-hour production, which hilariously blends stand-up comedy, lip sync, live music and a comic “op-ed” from the avian puppet Chad the Bird in a historic jazz club.
Post-pandemic, magic has flourished at the Rhapsody Theater in Rogers Park. I trekked up to that far North Side neighborhood to catch a Saturday-evening show in the 1912-vintage theater restored in 2022, by Ricardo Rosenkranz, a local physician and magician who performs there often (tickets start at around $30, but often go for $20 at the discount seller HotTix).
Chicago is known as the home of improv comedy, with Second City as its flagship. But there are many budget alternatives, including my Sunday-evening choice, “The Infinite Wrench,” from the improv company Neo-Futurists in the Andersonville neighborhood ($20 admission or “pay what you can,” starting at $1).
At 10:30 on Friday and Saturday nights and 7 p.m. on Sundays, the show promises 30 original plays — or sketches — in 60 minutes, or as many as they can get to as the clock winds down; that night they got to 28.
Its conclusion timed perfectly with the start of an 8:30 p.m. set of free music Sunday evenings — I caught a Western swing band, but programming varies weekly — around the corner at Simon’s Tavern, a neighborhood landmark since the 1930s.
Weekdays are prime times for free stand-up shows, which is how I discovered Pizza Mic at Pizzeria Serio in Roscoe Village on a Tuesday evening (free, including the pizza). Skewed to queer comics and hosted by Rey Tang, a transgender comic, the showcase attracts performers working on new material.
“This is a safe space to fail,” she said.
A neighborhood tour
One option for thrifty visitors: A neighborhood tour of Hyde Park, which was its own town and a retreat of the rich before being roped into Chicago in time for the 1893 World’s Fair.
Credit...Michelle Litvin for The New York Times
The suggestion to get out of downtown for savings applies to attractions, too. The Art Institute of Chicago costs $32, but the National Museum of Mexican Art in Pilsen and the Institute for the Study of Ancient Cultures in Hyde Park are free (the latter has a suggested admission of $10).
From downtown, I took the Metra electric train ($3.75) to reach the South Side neighborhood of Hyde Park, which is not on the L system.
Arriving in the leafy neighborhood of ornate mansions, I felt as if I’d left the city, which is historically accurate. Hyde Park was its own town and a retreat of the rich before being roped into Chicago in time for the 1893 World’s Fair, which was staged in the area.
“Hyde Park is an integrated space in what can be a very segregated city,” said Shermann Dilla Thomas, a Chicago historian who guides neighborhood tours on the South Side.
Not far from where the Obama Presidential Center is under construction, I met Laurie McGovern Petersen, the editor of the “ AIA Guide to Chicago,” from the American Institute of Architects Chicago, for a walk around Hyde Park.
Frank Lloyd Wright’s Prairie-style Robie House, in Hyde Park.
Credit...Michelle Litvin for The New York Times
“Hyde Park really has every style of architecture, from the 1850s to contemporary examples,” Ms. Petersen said. “It’s particularly rich in residential architecture.”
We meandered for hours, taking in blocks of Queen Anne mansions, Modernist townhouses from the architects Harry Weese and I.M. Pei, and the Prairie-style Robie House from Frank Lloyd Wright.
A visitor views Assyrian exhibits at the Institute for the Study of Ancient Cultures at the University of Chicago in Hyde Park.
Credit...Michelle Litvin for The New York Times
We parted ways at the University of Chicago’s main neo-Gothic campus. It includes the Institute for the Study of Ancient Cultures, which is filled with archaeological treasures, including a recreated courtyard from an eighth century B.C. Assyrian palace with an imposing relief sculpture of a winged bull that has a human head.
Before leaving Hyde Park, I stopped at Valois Restaurant, a 103-year-old cafeteria known to be a favorite of Barack Obama, who still owns a house nearby (the menu highlights a list of “President Obama’s Favorites”). My baked chicken with mashed potatoes and peas cost $9.45.
Animal house
African antelopes, known as klipspringers, at Chicago’s Lincoln Park Zoo.
Credit...Michelle Litvin for The New York Times
On my last day as a tourist, I grabbed a Divvy bicycle from the city’s shared bike program ($1 plus 18 cents per minute) and rode north toward my home, taking part of the 18-mile Lakefront Trail that borders Lake Michigan, passing beaches and parks.
Within a few miles, I reached the Lincoln Park Zoo. Its free admission seems to encourage locals as well as visitors to make repeat visits and develop relationships with the animals. The great apes and the lion pride draw regulars, who know their names and personalities.
I’m partial to the delicate African antelopes known as klipspringers, another entry on my rich list of Chicago freebies.
Elaine Glusac is the Frugal Traveler columnist, focusing on budget-friendly tips and journeys.
36 Hours in Chicago
Cycle miles of urban trails, tour a restored Frank Lloyd Wright masterwork and catch golden hour along Lake Michigan.
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