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5 Days in Chicago: A Journey of Flavors and Sights

Rosanette Ortiz

Rosanette Ortiz

4 Nov 2023

Experience the best of Chicago's culinary scene and iconic landmarks in this 5-day itinerary for solo travelers.

Trip to Chicago

Day 1
+

$156

Peet's Coffee and Tea
7:30 AM - 8:30 AM
•
$32
3 - 4 min

~

Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
9:00 AM - 10:00 AM
•
Free
3 - 4 min

~

Directions

The Purple Pig
1:00 PM - 2:30 PM
•
$72
3 - 4 min

~

Directions

Doc B's Fresh Kitchen River North
7:00 PM - 8:30 PM
•
$52
Day 2
+

$184

Wildberry Pancakes & Cafe
7:30 AM - 8:30 AM
•
$60
5 - 8 min

~

Directions

Maggie Daley Park Ice Skating Ribbon
Wide ice-skating track snaking around a rock-climbing facility in a park overlooked by skyscrapers.
9:00 AM - 10:30 AM
•
Free
6 - 9 min

~

Directions

Giordano's
Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.
1:00 PM - 2:30 PM
•
$48
13 - 20 min

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Directions

Robert's Pizza and Dough Company
7:00 PM - 8:30 PM
•
$76
Day 3
+

$172

Osaka Sushi Express & Fresh Fruit Smoothies
7:30 AM - 8:30 AM
•
$28
8 - 11 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
9:00 AM - 10:00 AM
•
Free
10 - 15 min

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Directions

Grant Park Bistro
1:00 PM - 2:30 PM
•
$48
11 - 16 min

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Directions

Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$96
Day 4
+

$297

Doc B's Fresh Kitchen
7:30 AM - 8:30 AM
•
$48
7 - 10 min

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Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
9:00 AM - 10:30 AM
•
$125
4 - 5 min

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Directions

Cafecito
1:00 PM - 2:30 PM
•
$72
8 - 11 min

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Directions

Do-Rite Donuts & Chicken
7:00 PM - 8:30 PM
•
$52
Day 5
+

$216

·

$ 10

Damn Fine Coffee Bar
7:30 AM - 8:30 AM
•
$40
12 - 18 min

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Directions

The 606
Created on a former rail line, this elevated, 2.7 mile landscaped trail draws runners & bikers.
9:00 AM - 10:30 AM
•
Free
5 - 6 min

~

Directions

Wyler Road
We offer a unique take on the neighborhood sandwich shop, focused on house-made, locally sourced ingredients, served in a modern but casual environment.
1:00 PM - 2:30 PM
•
$96
14 - 21 min

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Directions

Giant
7:00 PM - 8:30 PM
•
$80

Budget breakdown: $1035 In total

Activities & Food:$1025
Transport:$10