Cheap things to do in Chicago
Italian beef, jazz rooms, tacos and parks: the city on a tight budget.
This is Chicago for people who would rather spend money on a second round than on a tasting menu. Three days move from the Loop's free architecture and lore-soaked dive bars through Andersonville's Vietnamese counters and a legendary jazz room, finishing in Wicker Park and Logan Square with smash burgers, birria and a proper local bar. It works best if you like walking, eating at counters and leaving places before the cover charge kicks in.
Day 1: The Loop, the River, the lore
A day built around free architecture, a Tiffany dome most people walk past, and two of the cheapest iconic meals the city has ever produced.
- 9:30 AM
- 10:15 AM
Chicago Riverwalk
Free walk along the river's south bank under the bridges and towers, past the boat-tour docks.
Map - 12:30 PM
Mr. Beef
Legendary Italian beef sandwich in River North, cheap, iconic, cash-and-counter Chicago institution.
Map - 2:00 PM
Chicago Cultural Center
Free entry, world's largest Tiffany glass dome, most tourists walk past without knowing it's there.
Map - 7:30 PM
Billy Goat Tavern (The Original)
The original tavern under Michigan Avenue: cheezborgers, cheap beer and old newspaper lore.
Map - 9:00 PM
Day 2: Andersonville, Uptown, the Green Mill
A slow north-side day: Swedish museums, no-frills Vietnamese, birria from the essentials list, and a 1914 jazz room for the price of a beer.
- 9:30 AM
Rivers & Roads Cafe
Neighbourhood cafe on Devon Avenue for a coffee before heading south to Andersonville.
Map - 10:30 AM
Swedish American Museum
Free (or very cheap) neighbourhood museum, a genuinely quirky local culture stop in the heart of Andersonville.
Map - 12:30 PM
Nhà Hàng Vietnam Restaurant
Cheap, top-rated Vietnamese in Uptown, exactly the kind of no-frills lunch the neighbourhood does best.
Map - 2:00 PM
Welles Park
Free neighbourhood park, a relaxed afternoon walk to shake off lunch before the evening.
Map - 5:30 PM
Birrieria Zaragoza Uptown
Jalisco-style goat birria in consommé with fresh tortillas; cheap, rich, and next door to the Green Mill.
Map - 9:00 PM
The Green Mill
The Green Mill: a 1914 jazz room, once a Capone hangout, cash-conscious and gloriously unrenovated, the perfect cheap nightcap right on your doorstep.
Map
Day 3: Wicker Park to West Town
Espresso, a trail walk, smash burgers and punchy tacos before a final round at a no-nonsense local bar.
- 9:30 AM
- 10:15 AM
Wicker Park
Small triangle park at the heart of the neighbourhood, with a Victorian fountain and a dog run.
Map - 12:30 PM
Small Cheval- Wicker Park
Highly rated cheap smash burgers, exactly what a thrifty traveller wants for lunch.
Map - 2:00 PM
Bloomingdale Trail Park
The 606: an old elevated rail line turned 2.7-mile trail; walk a stretch east toward Bucktown.
Map - 7:30 PM
- 9:00 PM
Where to stay
The Hotel at Midtown
Sits between Bucktown and Logan Square, close to Day 3's trail and taquerias.
Fieldhouse Jones
Fieldhouse Jones is in River North, which anchors Day 1 and puts you on the Blue Line for Wicker Park on Day 3.
Make Chicago your trip
Swearby drafts the days from places people swear by. Swap any stop, then invite the crew by text, even friends without the app. Vote on dates, track costs as you go, and everyone gets one number at the end.
Get Swearby on the App StoreBefore you go
Book ahead
- Chicago Architecture Center River Cruise aboard First Lady: a few days ahead
- Art Institute of Chicago: a few days ahead
- Wrigley Field: a few days ahead
- The Second City: a few days ahead
- Kingston Mines: a few days ahead
- Heli Chicago: weeks ahead
Skip these
- Navy Pier, a long pier of chain food and souvenir markup. Go only for the wheel view or the summer fireworks from the lakefront.
- Giordano's or Uno as the pizza pilgrimage. Pequod's is the local pick and Lou Malnati's the classic deep dish alternative.
- Doing both observation decks, especially in rain or fog. Pick one deck on a clear day or spend the money on the river cruise.
- Magnificent Mile chain shopping at flagship prices, and eating deep dish more than once. Once, shared and sit down, is the experience.
The full Chicago travel guide: when to go, safety, getting around