10 Days in the Windy City!

J Oe

5 Dec 2023

Join me on an epic 10-day adventure through the vibrant streets of Chicago! From iconic landmarks to mouthwatering cuisine, this blog will take you on a whirlwind tour of the city's best attractions. Get ready for an unforgettable journey filled with culture, history, and delicious deep-dish pizza!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Theatres, Pancakes, and Pizza Galore!

$153

$ 3

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

8 - 11 min

Directions

Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.

No time set

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$32

8 - 11 min

Directions

1:00 PM - 2:30 PM

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$36

2 - 3 min

Directions

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.

7:00 PM - 8:30 PM

•

$28

3 - 4 min

Directions

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

11:30 AM - 12:30 PM

•

Free

5 - 8 min

Directions

French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.

9:00 AM - 10:00 PM

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$38

2 - 3 min

Directions

7:30 AM - 8:30 AM

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$19

Day 2Bridges, Parks, and Conservatories

$86

$ 13

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

13 - 16 min

Directions

Travelle at The Langham, Chicago is located on the second floor of the award-winning hotel. Travelle features a contemporary interpretation of Seasonal American cuisine. Drawing inspiration from the country’s rich culinary history, the kitchen takes guests on a culinary journey that includes ingr...

7:30 AM - 8:30 AM

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$23

5 - 8 min

Directions

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

9:00 AM - 10:00 AM

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Free

24 - 29 min

Directions

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

10:30 AM - 12:30 PM

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Free

9 - 14 min

Directions

1:00 PM - 2:30 PM

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$28

8 - 10 min

Directions

Garfield Park Conservatory - Reservations Required

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

2:30 PM - 4:00 PM

•

Free

12 - 15 min

Directions

Neighborhood tavern offering quality cocktails, spirits, beer, & wine.

7:00 PM - 8:30 PM

•

$35

Day 3Art, Fountains, and Millennium Park

$89

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

11 - 16 min

Directions

7:30 AM - 8:30 AM

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$21

4 - 5 min

Directions

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

9:00 AM - 11:00 AM

•

Free

2 - 3 min

Directions

Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.

11:30 AM - 12:30 PM

•

Free

4 - 6 min

Directions

We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.

1:00 PM - 2:30 PM

•

$32

3 - 4 min

Directions

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

2:30 PM - 3:30 PM

•

Free

4 - 6 min

Directions

7:00 PM - 8:30 PM

•

$36

Day 4Museums, Diners, and Pizza Cravings

$78

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

8 - 11 min

Directions

YOLK, created by founder Taki Kastanis in 2006, has evolved into Chicago's #1 breakfast hot spot. Follow us on Twitter and Instagram @EatYolk #EatYolk

7:30 AM - 8:30 AM

•

$22

10 - 15 min

Directions

57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.

9:00 AM - 12:00 PM

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Free

11 - 16 min

Directions

1:00 PM - 2:30 PM

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$29

5 - 8 min

Directions

Full-service restaurant.

7:00 PM - 8:30 PM

•

$27

Day 5Healthy Eats, Science, and Cafes

$118

$ 10

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

16 - 20 min

Directions

Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils

7:30 AM - 8:30 AM

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$25

8 - 11 min

Directions

Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.

9:00 AM - 1:00 PM

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$38

5 - 6 min

Directions

1:30 PM - 3:00 PM

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$29

6 - 8 min

Directions

7:00 PM - 8:30 PM

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$26

Day 6Asian Delights, Museums, and Pizza Cravings

$103

$ 8

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

11 - 14 min

Directions

7:30 AM - 8:30 AM

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$18

5 - 8 min

Directions

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

9:00 AM - 10:30 AM

•

Free

10 - 12 min

Directions

State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.

11:00 AM - 2:00 PM

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$31

8 - 10 min

Directions

Welcome to Chicago Curry House Indian Restaurant, an Indian and Nepalese dining concept here in the middle of Chicago. It is our little effort to bring you the taste of home cooked food from the huts of Rural India. Our recipes are very simple in nature but authentic in Indian flavor...

2:30 PM - 4:00 PM

•

$26

3 - 4 min

Directions

Full-service restaurant.

7:00 PM - 8:30 PM

•

$27

Day 7Subs, Fountains, and Legendary Music

$86

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

5 - 8 min

Directions

We have been serving our delicious subs, soups and salads for over 50 Years! We will continue to do so along with a few new additions to the Fontano’s menu. ...

7:30 AM - 8:30 AM

•

$21

8 - 11 min

Directions

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

9:00 AM - 10:00 AM

•

Free

4 - 5 min

Directions

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

10:30 AM - 12:30 PM

•

Free

7 - 10 min

Directions

Visit Buddy Guy's Legends to experience the finest blues seven nights a week, enjoy southern Cajun soul food, and behold a major archive of blues.

1:00 PM - 2:30 PM

•

$29

12 - 18 min

Directions

7:00 PM - 8:30 PM

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$36

Day 8Parks, Zoos, and Mediterranean Delights

$92

$ 8

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

18 - 22 min

Directions

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

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$25

8 - 12 min

Directions

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

9:00 AM - 11:00 AM

•

Free

18 - 22 min

Directions

Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.

11:30 AM - 1:30 PM

•

Free

6 - 9 min

Directions

By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas

2:00 PM - 3:30 PM

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$36

8 - 11 min

Directions

7:00 PM - 8:30 PM

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$31

Day 9Brunch, Baseball, and Sky-High Views

$246

$ 8

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

24 - 29 min

Directions

7:30 AM - 8:30 AM

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$20

6 - 9 min

Directions

Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.

9:00 AM - 12:00 PM

•

$132

17 - 21 min

Directions

12:30 PM - 2:00 PM

•

$31

5 - 8 min

Directions

Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.

2:00 PM - 3:30 PM

•

$31

6 - 9 min

Directions

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.

7:00 PM - 8:30 PM

•

$31

Day 10Tasty Pork, Skyline Views, and Pier Fun

$124

$ 5

Travelodge by Wyndham Downtown Chicago

Depart from your stay 🏨

9 - 14 min

Directions

Blends the bold flavors + savory spices found in Puerto Rico, South East Asia, China, Japan and Korea. Comfort foods from the motherland with a twist.

7:30 AM - 8:30 AM

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$24

5 - 8 min

Directions