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Chicago Adventure: 5 Days of Food and Fun

Kawika Villanueva

Kawika Villanueva

21 Oct 2023

Embark on a thrilling 5-day journey through the vibrant city of Chicago, indulging in delicious meals and exploring iconic landmarks. Join us as we uncover the best breakfast spots, visit famous attractions, and savor mouthwatering dinners at renowned restaurants.

Trip to Chicago

Day 1
+

$351

Torali
Savor authentic Italian cuisine in Chicago when dining at Torali. Located at the Ritz-Carlton, Chicago, our modern restaurant features contemporary dishes with local flair that will enlighten your dining experience.
7:30 AM - 8:30 AM
•
$68
3 - 4 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
•
$63
3 - 4 min

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Directions

Francesca's on Chestnut
1:00 PM - 2:30 PM
•
$102
3 - 4 min

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Directions

Rosebud Steakhouse
7:00 PM - 8:30 PM
•
$118
Day 2
+

$377

Metropolitan Club
7:30 AM - 8:30 AM
•
$76
1 - 2 min

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Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
9:00 AM - 10:30 AM
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$63
4 - 5 min

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Directions

The Florentine
Located in the bustling Loop on the 2nd floor of the JW Marriott Chicago, The Florentine showcases modern, seasonal Italian cuisine, in a warm, inviting environment. Characterized by elegant simplicity and paramount ingredients, the chef-driven menu boasts an extensive selection of classic antip...
1:00 PM - 2:30 PM
•
$128
4 - 5 min

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Directions

Boleo
Bringing a rooftop oasis to the Chicago skyline, we invite you to enjoy a night filled with refreshing cocktails, food with a Peruvian flair and live music.
7:00 PM - 8:30 PM
•
$110
Day 3
+

$266

Maison Parisienne
7:30 AM - 8:30 AM
•
$56
11 - 16 min

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Directions

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
9:00 AM - 10:00 AM
•
Free
3 - 4 min

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Directions

Mon Ami Gabi
1:00 PM - 2:30 PM
•
$114
6 - 9 min

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Riccardo Trattoria
7:00 PM - 8:30 PM
•
$96
Day 4
+

$294

FireLake Grill House and Cocktail Bar
Whether you’re looking for a dozen oysters fresh from the sea, a hearty weekend brunch buffet to enjoy with the kids or an elegant dinner starting with housemade pasta and ending with a slice of indulgent chocolate layered cake, we have you covered at Filini. We hope you’ve come hungry…
7:30 AM - 8:30 AM
•
$78
7 - 10 min

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Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
9:00 AM - 11:00 AM
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Free
4 - 6 min

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Directions

Ocean Prime
Ocean Prime is an award winning modern American restaurant and lounge from renowned restaurateur Cameron Mitchell. With stunning settings, a vibrant energy, an impressive menu of seafood and steaks and truly exceptional service, Ocean Prime is an ideal place to socialize, talk business, celebrate...
1:00 PM - 2:30 PM
•
$116
5 - 8 min

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Directions

The Terrace at Trump
7:00 PM - 8:30 PM
•
$100
Day 5
+

$369

Staytion Market & Bar
7:30 AM - 8:30 AM
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$80
2 - 3 min

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The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
9:00 AM - 11:00 AM
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$75
3 - 4 min

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Directions

Fisk & Co
Fisk & Co blends the vibe of Belgium’s lively bistros with the spirit of Chicago’s historic restaurant industry.
1:00 PM - 2:30 PM
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$102
4 - 5 min

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Directions

Catch 35
Catch 35 delivers ocean FRESH seafood to Chicagoland with offerings like Alaskan Halibut, Block Island Swordfish, Chilean Sea Bass & Prime bone-in Ribeyes.
7:00 PM - 8:30 PM
•
$112

Budget breakdown: $1656 In total

Activities & Food:$1656