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A Week in Chicago: Exploring the Windy City's Hidden Gems

Patricia Vargas Cedillo

3 Oct 2023

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Embark on a thrilling 7-day adventure in Chicago, uncovering its vibrant culture, stunning architecture, and mouthwatering cuisine. Discover the city's best-kept secrets and immerse yourself in its rich history. From iconic landmarks to charming parks, this itinerary has it all.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

+

$94

·

$ 15

Flying Saucer

7:30 AM - 8:30 AM

•

$38

9 - 14 min

~

Directions

Humboldt (Alexander Von) Park

Suburban recreational area with soccer & baseball fields, tennis courts & playgrounds, plus a beach.

9:00 AM - 11:00 AM

•

Free

6 - 8 min

~

Directions

Garfield Park Conservatory - Reservations Required

184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.

11:30 AM - 1:00 PM

•

Free

17 - 21 min

~

Directions

National Museum of Mexican Art

Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.

1:30 PM - 3:00 PM

•

Free

5 - 6 min

~

Directions

Azul 18

Discover all that Azul 18 has to offer by dining in or ordering take-out or delivery. Indulge in New American cuisine with a Latin twist at our Pilsen-area eatery. Also make sure to take advantage of FREE parking when you dine-in. with caramelized banana, salted caramel sauce and whipped butter. ...

7:00 PM - 8:30 PM

•

$56

Day 2

+

$116

NoMI

NoMI Kitchen. Long considered one of downtown Chicago's best restaurants, NoMI is a casually elegant dining destination for locals and hotel guests alike.

7:30 AM - 8:30 AM

•

$46

4 - 6 min

~

Directions

Holy Name Cathedral

An 1800s Catholic church with a vaulted ceiling & colorful stained glass, offering guided tours.

9:00 AM - 10:00 AM

•

Free

10 - 15 min

~

Directions

The Wrigley Building

Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.

10:30 AM - 11:30 AM

•

Free

2 - 3 min

~

Directions

DuSable Bridge

Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.

12:00 PM - 1:00 PM

•

Free

12 - 17 min

~

Directions

The Merchandise Mart

Huge building featuring high-end home design & furniture showrooms, plus a lineup of trade shows.

1:30 PM - 2:30 PM

•

Free

9 - 14 min

~

Directions

Civic Opera House

North America's 2nd-largest opera venue has over 3,500 seats & houses the Lyric Opera of Chicago.

3:00 PM - 4:30 PM

•

Free

8 - 12 min

~

Directions

Proxi

7:00 PM - 8:30 PM

•

$70

Day 3

+

$98

Ranalli's Lincoln Park

The Ranalli's family-owned business has been keeping Chicagoans well-fed for over 30 years. Starting on Lincoln Avenue in the 1970s, Ranalli's legendary food and around the world beer list, along with its famous outdoor patio, has become a favorite of both locals and tourists alike.

7:30 AM - 8:30 AM

•

$42

8 - 11 min

~

Directions

Nature Boardwalk at Lincoln Park Zoo

Prairie-style garden with trails, filled with native plants & home to birds, frogs & other wildlife.

9:00 AM - 10:00 AM

•

Free

8 - 11 min

~

Directions

Lincoln Park Zoo

Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.

10:30 AM - 12:30 PM

•

Free

5 - 8 min

~

Directions

Lincoln Park Conservatory

Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.

1:00 PM - 2:00 PM

•

Free

12 - 17 min

~

Directions

Oz Park

Oz-themed playground/park with statues of the Tin Man, Scarecrow, Cowardly Lion & Dorothy.

2:30 PM - 3:30 PM

•

Free

7 - 10 min

~

Directions

Café Ba-Ba-Reeba

7:00 PM - 8:30 PM

•

$56

Day 4

+

$98

·

$ 15

The Original Pancake House

7:30 AM - 8:30 AM

•

$44

6 - 8 min

~

Directions

Bahá'í House of Worship

Baha'i temple, one of 8 in the world, featuring a 135-ft white-stone dome completed in 1953.

9:00 AM - 10:30 AM

•

Free

32 - 39 min

~

Directions

North Avenue Beach

11:00 AM - 1:00 PM

•

Free

8 - 10 min

~

Directions

Ohio Street Beach

Sandy, north-facing public beach on Lake Michigan, popular for open-water swimming & skyline views.

1:30 PM - 3:30 PM

•

Free

6 - 9 min

~

Directions

Cupitol Coffee & Eatery

Cupitol is a new all-day​ lounge that brings together the best elements of a restaurant, a bakery, a cafe and an exclusive bar.

7:00 PM - 8:30 PM

•

$54

Day 5

+

$102

Cherry Circle Room

7:30 AM - 8:30 AM

•

$50

4 - 5 min

~

Directions

Crown Fountain

Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.

9:00 AM - 10:00 AM

•

Free

3 - 4 min

~

Directions

Millennium Park

24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.

10:30 AM - 12:30 PM

•

Free

8 - 11 min

~

Directions

Jay Pritzker Pavilion

Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.

1:00 PM - 2:00 PM

•

Free

10 - 15 min

~

Directions

Tribune Tower

Neo-Gothic skyscraper influenced by Rouen Cathedral & decorated with rocks from world landmarks.

2:30 PM - 3:30 PM

•

Free

2 - 3 min

~

Directions

The Purple Pig

7:00 PM - 8:30 PM

•

$52

Day 6

+

$90

·

$ 15

Eggy's Diner Chicago

Don’t be fooled by the name, Eggy’s is more than just breakfast (though it does have an extensive egg-centric menu). Modeled after the homey diners of the ‘60s, the menu is full of items designed to give a home-cooked feel. Think pancakes, grilled cheese sandwiches and burgers...

7:30 AM - 8:30 AM

•

$36

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

14 - 17 min

~

Directions

Ping Tom Memorial Park

Chinatown park on the Chicago River with Chinese-style landscaping, a playground & kayak rentals.

11:00 AM - 12:30 PM

•

Free

14 - 17 min

~

Directions

Jackson (Andrew) Park

540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.

1:00 PM - 3:00 PM

•

Free

7 - 9 min

~

Directions

Plein Air Cafe & Eatery

7:00 PM - 8:30 PM

•

$54

Day 7

+

$114

·

$ 5

Mercat a la Planxa

Take a culinary tour of Barcelona right on Michigan Avenue at Mercat a la Planxa, a Chicago Tapas Restaurant by Iron Chef Jose Garces!

7:30 AM - 8:30 AM

•

$42

5 - 8 min

~

Directions

Grant Park

312-acre centerpiece of Downtown housing some of the city's busiest attractions.

9:00 AM - 11:00 AM

•

Free

4 - 5 min

~

Directions

Buckingham Fountain

Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.

11:30 AM - 12:30 PM

•

Free

7 - 9 min

~

Directions

Chicago Cultural Center

Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.

1:00 PM - 2:00 PM

•

Free

4 - 5 min

~

Directions

Wildberry Pancakes & Cafe

7:00 PM - 8:30 PM

•

$72

Budget breakdown: $762 In total

Activities & Food:$712

Transport:$50