Worth the spend, plus the free and near-free wins.

1.Pilsen Murals & 18th StreetOn a budget, Pilsen Murals & 18th Street still earns its price.
2.Millennium Park & Cloud Gate (The Bean)On a budget, Millennium Park & Cloud Gate (The Bean) still earns its price.
3.Garfield Park ConservatoryOn a budget, Garfield Park Conservatory still earns its price.
4.Jackson Park & Garden of the PhoenixOn a budget, Jackson Park & Garden of the Phoenix still earns its price.
5.Starved Rock State Park (day-trip)On a budget, Starved Rock State Park (day-trip) still earns its price.
6.Lakefront TrailOn a budget, Lakefront Trail still earns its price.
7.Chicago Cultural CenterOn a budget, Chicago Cultural Center still earns its price.
8.Chicago Architecture River CruiseOn a budget, Chicago Architecture River Cruise still earns its price.
9.ChinatownOn a budget, Chinatown still earns its price.
10.Girl & the GoatOn a budget, Girl & the Goat still earns its price.
11.Green Mill Jazz ClubOn a budget, Green Mill Jazz Club still earns its price.
12.The Loop & the 'L'On a budget, The Loop & the 'L' still earns its price.
13.Lincoln ParkOn a budget, Lincoln Park still earns its price.
14.Logan SquareOn a budget, Logan Square still earns its price.
15.Wicker Park / BucktownOn a budget, Wicker Park / Bucktown still earns its price.
16.Chicago Architecture Walking TourOn a budget, Chicago Architecture Walking Tour still earns its price.
17.Art Institute of ChicagoOn a budget, Art Institute of Chicago still earns its price.
18.Hyde ParkOn a budget, Hyde Park still earns its price.
19.Smoque BBQOn a budget, Smoque BBQ still earns its price.
20.Chicago RiverwalkOn a budget, weigh it — Chicago Riverwalk isn't cheap for what it is.
21.North Avenue BeachOn a budget, weigh it — North Avenue Beach isn't cheap for what it is.
22.Indiana Dunes (day-trip)On a budget, weigh it — Indiana Dunes (day-trip) isn't cheap for what it is.
23.Pequod's PizzaOn a budget, weigh it — Pequod's Pizza isn't cheap for what it is.
24.Old TownOn a budget, weigh it — Old Town isn't cheap for what it is.
25.MonteverdeOn a budget, weigh it — Monteverde isn't cheap for what it is.
26.Lincoln Park ZooOn a budget, weigh it — Lincoln Park Zoo isn't cheap for what it is.
27.Grant ParkOn a budget, weigh it — Grant Park isn't cheap for what it is.
28.Au ChevalOn a budget, weigh it — Au Cheval isn't cheap for what it is.
29.Milwaukee (day-trip)On a budget, weigh it — Milwaukee (day-trip) isn't cheap for what it is.
30.AlineaOn a budget, weigh it — Alinea isn't cheap for what it is.
31.Museum of Contemporary ArtOn a budget, weigh it — Museum of Contemporary Art isn't cheap for what it is.
32.Lou Malnati's PizzeriaOn a budget, weigh it — Lou Malnati's Pizzeria isn't cheap for what it is.
33.Buckingham FountainOn a budget, weigh it — Buckingham Fountain isn't cheap for what it is.
34.Chicago Athletic Association HotelOn a budget, weigh it — Chicago Athletic Association Hotel isn't cheap for what it is.
35.The 606 (Bloomingdale Trail)On a budget, weigh it — The 606 (Bloomingdale Trail) isn't cheap for what it is.
36.Deep-Dish Pizza CrawlOn a budget, weigh it — Deep-Dish Pizza Crawl isn't cheap for what it is.
37.360 Chicago (Hancock)On a budget, weigh it — 360 Chicago (Hancock) isn't cheap for what it is.
38.Field MuseumOn a budget, weigh it — Field Museum isn't cheap for what it is.
39.Museum CampusOn a budget, weigh it — Museum Campus isn't cheap for what it is.
40.The PublicanOn a budget, weigh it — The Publican isn't cheap for what it is.
41.Adler PlanetariumOn a budget, weigh it — Adler Planetarium isn't cheap for what it is.
42.The RobeyOn a budget, weigh it — The Robey isn't cheap for what it is.
43.Willis Tower SkydeckOn a budget, weigh it — Willis Tower Skydeck isn't cheap for what it is.
44.Ace Hotel ChicagoOn a budget, weigh it — Ace Hotel Chicago isn't cheap for what it is.
45.The Peninsula ChicagoOn a budget, weigh it — The Peninsula Chicago isn't cheap for what it is.
46.The Langham, ChicagoOn a budget, weigh it — The Langham, Chicago isn't cheap for what it is.
47.The Second CityOn a budget, weigh it — The Second City isn't cheap for what it is.
48.WrigleyvilleOn a budget, weigh it — Wrigleyville isn't cheap for what it is.
49.The Walnut RoomOn a budget, weigh it — The Walnut Room isn't cheap for what it is.
50.The Hoxton, ChicagoOn a budget, weigh it — The Hoxton, Chicago isn't cheap for what it is.
51.Four Seasons Hotel ChicagoOn a budget, weigh it — Four Seasons Hotel Chicago isn't cheap for what it is.
52.Museum of Science & IndustryOn a budget, weigh it — Museum of Science & Industry isn't cheap for what it is.
53.ChristkindlmarketOn a budget, weigh it — Christkindlmarket isn't cheap for what it is.
54.The Purple PigOn a budget, weigh it — The Purple Pig isn't cheap for what it is.Itineraries are prefiltered verdict lists — every spot is graded honestly, not pay-to-place.