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10 Days in Chicago: A Journey of Culture and Cuisine

Tolou Shokuhfar

Tolou Shokuhfar

5 Nov 2023

Embark on a 10-day adventure in Chicago, exploring its vibrant cultural landmarks and indulging in delicious cuisine. From the iconic Chicago Theatre to the hidden gems like the Garfield Park Conservatory, this itinerary promises an unforgettable experience.

Day 1
+

$26

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
8:00 AM - 9:00 AM
Free
6 - 9 min

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Directions

McCormick Bridgehouse & Chicago River Museum
Exhibits on the city's river & movable bridges & their significance to the city.
9:30 AM - 10:30 AM
Free
4 - 6 min

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Directions

The Purple Pig
7:00 PM - 8:30 PM
$26
Day 2
+

$101

·

$ 10

WNDR Museum
Multi-sensory, contemporary installations by artists including Yayoi Kusama.
8:00 AM - 9:30 AM
$63
22 - 27 min

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Directions

The 606
Created on a former rail line, this elevated, 2.7 mile landscaped trail draws runners & bikers.
10:00 AM - 11:30 AM
Free
5 - 6 min

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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.
7:00 PM - 8:30 PM
$38
Day 3
+

$48

·

$ 5

Garfield Park Conservatory - Reservations Required
184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.
8:00 AM - 9:30 AM
Free
18 - 22 min

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Directions

Civic Opera House
North America's 2nd-largest opera venue has over 3,500 seats & houses the Lyric Opera of Chicago.
10:00 AM - 11:30 AM
Free
6 - 9 min

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Directions

Hogsalt - Small C
7:00 PM - 8:30 PM
$48
Day 4
+

$76

Museum of Broadcast Communications
Thousands of historic radio & TV programs plus commercials comprise this 4-floor museum.
8:00 AM - 9:30 AM
Free
8 - 11 min

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Directions

The Richard H. Driehaus Museum
Restored 19th-century mansion with notable Gilded Age architectural features & antiques.
10:00 AM - 11:30 AM
$50
3 - 4 min

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Directions

Brightwok Kitchen
7:00 PM - 8:30 PM
$26
Day 5
+

$115

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
$75
4 - 5 min

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Directions

Roti Modern Mediterranean
By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas
7:00 PM - 8:30 PM
$40
Day 6
+

$97

·

$ 10

Jane Addams Hull-House Museum
Mansion where Jane Addams began the settlement-house movement & now a museum with exhibits & tours.
8:00 AM - 9:30 AM
Free
9 - 11 min

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Directions

The Rookery Building
Chicago's oldest high-rise, this 1888 Romanesque structure has a Frank Lloyd Wright-designed lobby.
10:00 AM - 11:00 AM
$38
20 - 24 min

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Directions

Institute for the Study of Ancient Cultures Museum
Dedicated to researching ancient civilizations of the Middle East & educating the public about them.
11:30 AM - 12:30 PM
$25
4 - 5 min

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Directions

Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
$34
Day 7
+

$97

·

$ 10

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
8:00 AM - 9:30 AM
$63
22 - 27 min

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Directions

Stony Island Arts Bank
10:00 AM - 11:00 AM
Free
9 - 11 min

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Directions

Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
$34
Day 8
+

$44

·

$ 5

Block Museum of Art, Northwestern University
Galleries of rotating fine-art exhibits, a diverse permanent collection, films & cultural programs.
8:00 AM - 9:30 AM
Free
25 - 30 min

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Directions

Swedish American Museum
Celebrating Nordic culture & history with various programs including exhibits, tours & a kids' area.
10:00 AM - 11:30 AM
Free
2 - 3 min

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Directions

Taste of Lebenon Restaurant
7:00 PM - 8:30 PM
$44
Day 9
+

$134

·

$ 5

Chicago Sports Museum
Interactive exhibits, artifacts & memorabilia help tell the story of the city's rich sports history.
8:00 AM - 9:30 AM
$50
21 - 26 min

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Directions

Frederick C. Robie House
Notable 1910 Prairie-style house designed by Frank Lloyd Wright, offering tours 5 days a week.
10:00 AM - 11:00 AM
$50
1 - 2 min

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Directions

Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
$34
Day 10
+

$78

·

$ 5

Museum Of Contemporary Art Chicago
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
8:00 AM - 9:30 AM
$38
16 - 20 min

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Directions

Hyde Park Art Center
Nonprofit visual arts center exhibiting work by emerging or under-recognized contemporary artists.
10:00 AM - 11:30 AM
Free
8 - 11 min

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Directions

Virtue Restaurant
7:00 PM - 8:30 PM
$40

Budget breakdown: $864 In total

Activities & Food:$814
Transport:$50