Chicago Riddles: Test Your Knowledge of the Windy City
Intro:
Welcome to Chicago Riddles — where the Windy City becomes the ultimate puzzle! 
Whether you’re a proud Chicagoan or a visitor exploring the city’s rich history and iconic landmarks, these riddles will test your knowledge and spark your curiosity. From the towering skyline to deep-dish pizza, get ready for some fun challenges about this famous city!
Windy City Wonders: Easy Chicago-Riddles-with-Answers
Simple riddles to kick off your Chicago adventure.
Riddles 1
Question:
I’m the tallest in Chicago, piercing the sky; what am I?
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Riddles 2
Question:
I’m deep and cheesy, a Windy City bite; what am I?
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Riddles 3
Question:
I’m the vast blue edge of the city’s shore; what am I?
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Riddles 4
Question:
I’m a shiny sculpture folks call a legume; what am I?
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Riddles 5
Question:
I’m a red beast charging on the court; what am I?
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Riddles 6
Question:
I’m the gust that gave the city its nickname; what am I?
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Riddles 7
Question:
I’m a waterway dyed green for a holiday cheer; what am I?
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Riddles 8
Question:
I’m a skyscraper once called Sears; what am I?
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Riddles 9
Question:
I’m a dish stacked high with sauce and crust; what am I?
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Riddles 10
Question:
I’m a freshwater giant along Michigan Avenue; what am I?
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Riddles 11
Question:
I’m a mirrored marvel in Millennium Park; what am I?
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Riddles 12
Question:
I’m a mascot slamming dunks at the United Center; what am I?
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Riddles 13
Question:
I’m a breeze that whips through the Loop; what am I?
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Riddles 14
Question:
I’m a stream flowing backward through the city; what am I?
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Riddles 15
Question:
I’m a high-rise with a view from 103 floors; what am I?
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Riddles 16
Question:
I’m a savory pie Chicagoans adore; what am I?
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Riddles 17
Question:
I’m the city’s liquid border to the east; what am I?
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Riddles 18
Question:
I’m a steel shape reflecting skyline dreams; what am I?
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Riddles 19
Question:
I’m a hoops legend tied to Jordan’s fame; what am I?
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Riddles 20
Question:
I’m a current that snakes past skyscrapers; what am I?
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Call to Action: Warmed up by these Windy City wonders? Share your favorite “Chicago-Riddle-with-Answer” with your crew and kick off a Chi-town riddle spree!
Pizza Party Puns: Funny Chicago-Riddles-with-Answers
Hilarious riddles to tickle your Chicago funny bone.
Riddles 21
Question:
I’m a tower that sways when the wind gets frisky; what am I?
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Riddles 22
Question:
I’m a pizza so thick it needs a forklift; what am I?
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Riddles 23
Question:
I’m a lake that freezes and makes you shiver; what am I?
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Riddles 24
Question:
I’m a bean that photobombs your selfies; what am I?
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Riddles 25
Question:
I’m a bull that dunks on your grandma; what am I?
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Riddles 26
Question:
I’m a wind that steals your hat in the Loop; what am I?
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Riddles 27
Question:
I’m a river that turns green and Irish; what am I?
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Riddles 28
Question:
I’m a tower too tall for short jokes; what am I?
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Riddles 29
Question:
I’m a pizza that laughs at thin crusts; what am I?
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Riddles 30
Question:
I’m a lake that waves at passing boats; what am I?
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Riddles 31
Question:
I’m a bean that mirrors your goofy grin; what am I?
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Riddles 32
Question:
I’m a bull that roars louder than fans; what am I?
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Riddles 33
Question:
I’m a wind that messes up your hairdo; what am I?
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Riddles 34
Question:
I’m a river that spills green dye yearly; what am I?
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Riddles 35
Question:
I’m a tower that brags about its height; what am I?
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Riddles 36
Question:
I’m a pizza too deep for shallow plates; what am I?
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Riddles 37
Question:
I’m a lake that splashes the shore silly; what am I?
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Riddles 38
Question:
I’m a bean that winks at tourists; what am I?
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Riddles 39
Question:
I’m a bull that slam-dunks the competition; what am I?
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Riddles 40
Question:
I’m a wind that howls like a bad singer; what am I?
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Call to Action: Cracked up by these pizza party puns? Toss your funniest “Chicago-Riddle-with-Answer” into the mix and keep the Chi-town chuckles rolling!
Lakefront Logic: Logical Chicago-Riddles-with-Answers
Smart riddles to puzzle out Chicago’s charm.
Riddles 41
Question:
I’m the structure that looms over the city’s core; what am I?
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Riddles 42
Question:
I’m the dish that layers sauce and cheese thick; what am I?
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Riddles 43
Question:
I’m the water that borders Chicago’s east; what am I?
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Riddles 44
Question:
I’m the art piece that reflects the skyline’s glow; what am I?
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Riddles 45
Question:
I’m the emblem of hoops glory in red; what am I?
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Riddles 46
Question:
I’m the force that sweeps through the streets; what am I?
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Riddles 47
Question:
I’m the channel that flows through downtown; what am I?
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Riddles 48
Question:
I’m the edifice with a deck at 1,353 feet; what am I?
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Riddles 49
Question:
I’m the meal that’s a pan of pure delight; what am I?
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Riddles 50
Question:
I’m the expanse touching Navy Pier’s edge; what am I?
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Riddles 51
Question:
I’m the sculpture that warps the city’s face; what am I?
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Riddles 52
Question:
I’m the team tied to six championship rings; what am I?
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Riddles 53
Question:
I’m the air that dances with the flags; what am I?
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Riddles 54
Question:
I’m the waterway engineered to reverse; what am I?
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Riddles 55
Question:
I’m the high point of Chicago’s skyline; what am I?
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Riddles 56
Question:
I’m the cuisine that’s a deep-dish dream; what am I?
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Riddles 57
Question:
I’m the shore that stretches north and south; what am I?
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Riddles 58
Question:
I’m the metallic marvel kids climb under; what am I?
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Riddles 59
Question:
I’m the mascot of a dynasty in red and black; what am I?
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Riddles 60
Question:
I’m the stream that splits the city’s heart; what am I?
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Call to Action: Solved these lakefront logic puzzles? Share these “Chicago-Riddles-with-Answers” with your brainy Chicago buddies and crack the city’s code!
Bean Bafflers: Tricky Chicago-Riddles-with-Answers
Clever riddles to twist your Chicago mind.
Riddles 61
Question:
I soar with a twist, a height assist; what am I?
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Riddles 62
Question:
I stack with a grin, a crust within; what am I?
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Riddles 63
Question:
I lap with a wink, a shore I link; what am I?
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Riddles 64
Question:
I gleam with a jest, a shape my quest; what am I?
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Riddles 65
Question:
I charge with a trick, a dunk so quick; what am I?
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Riddles 66
Question:
I blow with a twist, a gust assist; what am I?
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Riddles 67
Question:
I flow with a grin, a dye within; what am I?
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Riddles 68
Question:
I rise with a wink, a deck I link; what am I?
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From Riddle Palace
Riddles 69
Question:
I pile with a jest, a sauce my quest; what am I?
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From Riddle Palace
Riddles 70
Question:
I stretch with a twist, a wave assist; what am I?
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From Riddle Palace
Riddles 71
Question:
I shine with a grin, a curve within; what am I?
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From Riddle Palace
Riddles 72
Question:
I roar with a wink, a hoop I link; what am I?
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From Riddle Palace
Riddles 73
Question:
I howl with a jest, a breeze my quest; what am I?
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From Riddle Palace
Riddles 74
Question:
I wind with a trick, a green so quick; what am I?
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From Riddle Palace
Riddles 75
Question:
I loom with a grin, a view within; what am I?
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From Riddle Palace
Riddles 76
Question:
I bake with a twist, a cheese assist; what am I?
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From Riddle Palace
Riddles 77
Question:
I splash with a jest, a pier my quest; what am I?
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From Riddle Palace
Riddles 78
Question:
I warp with a wink, a steel I link; what am I?
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From Riddle Palace
Riddles 79
Question:
I slam with a grin, a ring within; what am I?
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From Riddle Palace
Riddles 80
Question:
I rush with a twist, a current assist; what am I?
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Call to Action: Baffled by these bean bafflers? Share these tricky “Chicago-Riddles-with-Answers” with a sly Chicagoan and unravel the Windy City’s twists!
Bull’s-Eye Brainteasers: Math-Based Chicago-Riddles-with-Answers
Numbered riddles to tally Chicago’s treasures.
Riddles 81
Question:
I’m 1 spire with 103 floors; what am I?
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Riddles 82
Question:
I’m 1 pie with 2 inches of cheese; what am I?
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Riddles 83
Question:
I’m 1 body with 3 million waves; what am I?
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Riddles 84
Question:
I’m 1 shape with 4 curves; what am I?
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Riddles 85
Question:
I’m 1 team with 6 rings; what am I?
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Riddles 86
Question:
I’m 1 gust with 5 puffs; what am I?
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Riddles 87
Question:
I’m 1 flow with 2 banks; what am I?
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Riddles 88
Question:
I’m 1 peak with 4 sides; what am I?
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Riddles 89
Question:
I’m 1 dish with 3 layers; what am I?
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Riddles 90
Question:
I’m 1 shore with 5 piers; what am I?
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Riddles 91
Question:
I’m 1 art with 2 tons; what am I?
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Riddles 92
Question:
I’m 1 mascot with 4 dunks; what am I?
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Riddles 93
Question:
I’m 1 breeze with 3 howls; what am I?
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Riddles 94
Question:
I’m 1 stream with 6 bridges; what am I?
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Riddles 95
Question:
I’m 1 height with 2 decks; what am I?
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Riddles 96
Question:
I’m 1 slice with 5 toppings; what am I?
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Riddles 97
Question:
I’m 1 expanse with 4 beaches; what am I?
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Riddles 98
Question:
I’m 1 curve with 3 reflections; what am I?
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Riddles 99
Question:
I’m 1 champ with 2 Jordans; what am I?
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Riddles 100
Question:
I’m 1 channel with 3 turns; what am I?
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Call to Action: Nailed these bull’s-eye brainteasers? Share these “Chicago-Riddles-with-Answers” with your math-savvy Chicago fans and count the city’s wins!
Towering Teasers: Bold Chicago-Riddles-with-Answers
Grand riddles to scale Chicago’s heights.
Riddles 101
Question:
I pierce the clouds with steel might; what am I?
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Riddles 102
Question:
I pile flavors in a pan so deep; what am I?
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Riddles 103
Question:
I stretch wide with waves of blue; what am I?
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Riddles 104
Question:
I shimmer bright in a park’s embrace; what am I?
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Riddles 105
Question:
I charge the court with fierce red pride; what am I?
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Riddles 106
Question:
I sweep the streets with gusty roar; what am I?
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Riddles 107
Question:
I carve the city with liquid grace; what am I?
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Riddles 108
Question:
I stand tall with a view so vast; what am I?
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Riddles 109
Question:
I bake bold in a Chicago oven; what am I?
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Riddles 110
Question:
I lap the shore with endless song; what am I?
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Riddles 111
Question:
I reflect the skyline in silver sheen; what am I?
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From Riddle Palace
Riddles 112
Question:
I dunk and soar in championship lore; what am I?
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Riddles 113
Question:
I howl through alleys with wild delight; what am I?
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Riddles 114
Question:
I flow reversed with emerald fame; what am I?
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Riddles 115
Question:
I scrape the sky with iron will; what am I?
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Riddles 116
Question:
I stack sauce high in Windy style; what am I?
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Riddles 117
Question:
I border the city with watery might; what am I?
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Riddles 118
Question:
I gleam in glory by the fountain’s spray; what am I?
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Riddles 119
Question:
I reign in red on hardwood floors; what am I?
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Riddles 120
Question:
I rush through bridges with urban flair; what am I?
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Call to Action: Scaled these towering teasers? Share these “Chicago-Riddles-with-Answers” with your bold Chicago crew and conquer the city’s heights!
River Rambles: Clever Chicago-Riddles-with-Answers
Witty riddles to navigate Chicago’s currents.
Riddles 121
Question:
I rise with a wink, a height I link; what am I?
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From Riddle Palace
Riddles 122
Question:
I stack with a jest, a crust my quest; what am I?
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From Riddle Palace
Riddles 123
Question:
I lap with a grin, a shore within; what am I?
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From Riddle Palace
Riddles 124
Question:
I gleam with a twist, a shape assist; what am I?
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From Riddle Palace
Riddles 125
Question:
I charge with a wink, a dunk I link; what am I?
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From Riddle Palace
Riddles 126
Question:
I blow with a jest, a gust my quest; what am I?
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From Riddle Palace
Riddles 127
Question:
I flow with a twist, a dye assist; what am I?
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From Riddle Palace
Riddles 128
Question:
I soar with a grin, a deck within; what am I?
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From Riddle Palace
Riddles 129
Question:
I pile with a wink, a sauce I link; what am I?
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From Riddle Palace
Riddles 130
Question:
I stretch with a jest, a wave my quest; what am I?
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From Riddle Palace
Riddles 131
Question:
I shine with a twist, a curve assist; what am I?
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From Riddle Palace
Riddles 132
Question:
I roar with a grin, a hoop within; what am I?
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From Riddle Palace
Riddles 133
Question:
I howl with a wink, a breeze I link; what am I?
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From Riddle Palace
Riddles 134
Question:
I wind with a jest, a green my quest; what am I?
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From Riddle Palace
Riddles 135
Question:
I loom with a twist, a view assist; what am I?
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From Riddle Palace
Riddles 136
Question:
I bake with a grin, a cheese within; what am I?
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From Riddle Palace
Riddles 137
Question:
I splash with a wink, a pier I link; what am I?
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From Riddle Palace
Riddles 138
Question:
I warp with a jest, a steel my quest; what am I?
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From Riddle Palace
Riddles 139
Question:
I slam with a twist, a ring assist; what am I?
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From Riddle Palace
Riddles 140
Question:
I rush with a grin, a current within; what am I?
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From Riddle Palace
Call to Action: Navigated these river rambles? Share these clever “Chicago-Riddles-with-Answers” with your sharp Chicago pals and flow through the city’s wit!
What’s My Chicago?: What Am I? Chicago-Riddles-with-Answers
Riddles asking “What Am I?” with Chicago flair.
Riddles 141
Question:
I’m the spire that towers where skies unwind; what am I?
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From Riddle Palace
Riddles 142
Question:
I’m the dish that stacks where flavors align; what am I?
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From Riddle Palace
Riddles 143
Question:
I’m the water that laps where shores entwine; what am I?
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From Riddle Palace
Riddles 144
Question:
I’m the shape that gleams where parks define; what am I?
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From Riddle Palace
Riddles 145
Question:
I’m the beast that dunks where rings refine; what am I?
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From Riddle Palace
Riddles 146
Question:
I’m the gust that blows where streets unwind; what am I?
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From Riddle Palace
Riddles 147
Question:
I’m the flow that winds where bridges align; what am I?
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From Riddle Palace
Riddles 148
Question:
I’m the peak that soars where heights entwine; what am I?
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From Riddle Palace
Riddles 149
Question:
I’m the pie that bakes where tastes define; what am I?
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From Riddle Palace
Riddles 150
Question:
I’m the expanse that waves where piers unwind; what am I?
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From Riddle Palace
Riddles 151
Question:
I’m the steel that shines where selfies align; what am I?
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From Riddle Palace
Riddles 152
Question:
I’m the champ that roars where fans entwine; what am I?
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From Riddle Palace
Riddles 153
Question:
I’m the breeze that howls where flags define; what am I?
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From Riddle Palace
Riddles 154
Question:
I’m the stream that dyes where green unwinds; what am I?
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From Riddle Palace
Riddles 155
Question:
I’m the deck that views where clouds align; what am I?
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From Riddle Palace
Riddles 156
Question:
I’m the crust that piles where cheese entwines; what am I?
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From Riddle Palace
Riddles 157
Question:
I’m the shore that stretches where waves define; what am I?
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From Riddle Palace
Riddles 158
Question:
I’m the art that curves where steel unwinds; what am I?
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From Riddle Palace
Riddles 159
Question:
I’m the mascot that slams where hoops align; what am I?
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From Riddle Palace
Riddles 160
Question:
I’m the current that flows where downtown entwines; what am I?
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From Riddle Palace
Call to Action: Guessed your Chicago? Share these “What Am I?” “Chicago-Riddles-with-Answers” with your Windy City squad and see who claims the Chi-town crown!
Windy Wordplay: Punny Chicago-Riddles-with-Answers
Punny riddles to gust through Chicago’s spirit.
Riddles 161
Question:
I “tower” over the town; what am I?
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From Riddle Palace
Riddles 162
Question:
I “pizza” the puzzle; what am I?
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From Riddle Palace
Riddles 163
Question:
I “lake” your breath away; what am I?
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From Riddle Palace
Riddles 164
Question:
I “bean” there, done that; what am I?
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From Riddle Palace
Riddles 165
Question:
I “bull” the shots; what am I?
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From Riddle Palace
Riddles 166
Question:
I “wind” your mind; what am I?
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From Riddle Palace
Riddles 167
Question:
I “river” your thoughts; what am I?
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From Riddle Palace
Riddles 168
Question:
I “tower” above the rest; what am I?
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From Riddle Palace
Riddles 169
Question:
I “pizza” you off; what am I?
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From Riddle Palace
Riddles 170
Question:
I “lake” it or leave it; what am I?
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From Riddle Palace
Riddles 171
Question:
I “bean” a big deal; what am I?
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From Riddle Palace
Riddles 172
Question:
I “bull” no punches; what am I?
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From Riddle Palace
Riddles 173
Question:
I “wind” you up; what am I?
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From Riddle Palace
Riddles 174
Question:
I “river” run deep; what am I?
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From Riddle Palace
Riddles 175
Question:
I “tower” with pride; what am I?
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From Riddle Palace
Riddles 176
Question:
I “pizza” the pie; what am I?
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From Riddle Palace
Riddles 177
Question:
I “lake” a big splash; what am I?
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From Riddle Palace
Riddles 178
Question:
I “bean” reflecting you; what am I?
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From Riddle Palace
Riddles 179
Question:
I “bull” the court; what am I?
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From Riddle Palace
Riddles 180
Question:
I “wind” through streets; what am I?
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From Riddle Palace
Riddles 181
Question:
I “river” your green; what am I?
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From Riddle Palace
Riddles 182
Question:
I “tower” your view; what am I?
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From Riddle Palace
Riddles 183
Question:
I “pizza” your plate; what am I?
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From Riddle Palace
Riddles 184
Question:
I “lake” the shore; what am I?
Whether you’re a hopeless romantic, a deep thinker, or just someone who loves a good challenge, these riddles will have you smiling, thinking, and maybe even feeling a little sentimental. Get ready to follow your heart — and your brain…
