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A Week in Chicago: Explore the Windy City's Best

Ana Isabel Treviño

Ana Isabel Treviño

9 Oct 2023

Embark on a thrilling 7-day journey through Chicago, IL, United States. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the vibrant culture of the Windy City.

Trip to Chicago

Day 1
+

$237

·

$ 10

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

5 - 8 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
5 - 8 min

~

Directions

Saucy Porka
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
•
$38
9 - 11 min

~

Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
9:00 AM - 11:00 AM
•
$63
9 - 14 min

~

Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
11:30 AM - 2:30 PM
•
Free
7 - 10 min

~

Directions

Yolk
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
3:00 PM - 4:30 PM
•
$72
Victory Tap
Serving traditional Italian food since 1956 with a passion for traditional Italian dishes has created our fine menu of tried and true classics sure to impress anyones pallet.
1:30 PM - 3:00 PM
•
$64
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 2
+

$229

·

$ 10

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

16 - 20 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
8 - 11 min

~

Directions

B'Gabs
Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils
7:30 AM - 8:30 AM
•
$46
16 - 20 min

~

Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
9:00 AM - 1:00 PM
•
$75
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
1:30 PM - 3:00 PM
•
$56
4 - 6 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
3:00 PM - 5:00 PM
•
Free
Cherry Circle Room
7:00 PM - 8:30 PM
•
$52
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 3
+

$325

·

$ 20

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

9 - 11 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
7 - 10 min

~

Directions

Lou Mitchell's Restaurant & Bakery
Lou Mitchell’s is not only a classic Chicago icon, but our food is recognized both nationally and internationally with endless accolades. Among the list are USA Today, American Way, newspapers, magazines, food critics, television. It’s a must see place.
7:30 AM - 8:30 AM
•
$42
17 - 21 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
9:00 AM - 10:30 AM
•
$63
12 - 15 min

~

Directions

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
11:00 AM - 1:00 PM
•
Free
16 - 23 min

~

Directions

Victory Tap
Serving traditional Italian food since 1956 with a passion for traditional Italian dishes has created our fine menu of tried and true classics sure to impress anyones pallet.
1:30 PM - 3:00 PM
•
$64
6 - 8 min

~

Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
3:00 PM - 6:00 PM
•
$100
Eleven City Diner
7:00 PM - 8:30 PM
•
$56
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 4
+

$298

·

$ 10

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

12 - 18 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
8 - 12 min

~

Directions

Burger Bar
American Ranchers know a thing or two about beef. When they tell us that Prime is the best, we just go with the flow and serve up the biggest, baddest Prime burgers around.
7:30 AM - 8:30 AM
•
$44
9 - 11 min

~

Directions

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
9:00 AM - 12:00 PM
•
$63
4 - 5 min

~

Directions

The Dearborn
Urban American tavern in Chicago's Block 37
12:30 PM - 2:00 PM
•
$58
4 - 5 min

~

Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
2:00 PM - 4:00 PM
•
$75
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
1:30 PM - 3:00 PM
•
$58
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 5
+

$223

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

7 - 10 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
5 - 8 min

~

Directions

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
•
$50
4 - 5 min

~

Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
9:00 AM - 11:00 AM
•
Free
12 - 17 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
4 - 5 min

~

Directions

The Gage
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
•
$58
4 - 6 min

~

Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
2:30 PM - 5:30 PM
•
$63
Cherry Circle Room
7:00 PM - 8:30 PM
•
$52
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 6
+

$305

·

$ 20

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

13 - 16 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
7 - 10 min

~

Directions

Doc B's Fresh Kitchen
7:30 AM - 8:30 AM
•
$36
9 - 11 min

~

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
14 - 17 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
11:00 AM - 1:00 PM
•
Free
6 - 9 min

~

Directions

PR Italian Bistro
Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago
1:30 PM - 3:00 PM
•
$52
11 - 16 min

~

Directions

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
3:00 PM - 6:00 PM
•
$100
The Chicago Diner, Lakeview
7:00 PM - 8:30 PM
•
$54
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
Day 7
+

$272

·

$ 20

Hotel Blake, an Ascend Hotel Collection Member

Depart from your stay 🏨

11 - 14 min

~

Directions

Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free
10 - 15 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.
7:30 AM - 8:30 AM
•
$42
6 - 8 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
9:00 AM - 11:00 AM
•
$63
5 - 6 min

~

Directions

Museum Of Contemporary Art Chicago
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
11:30 AM - 1:00 PM
•
$38
5 - 8 min

~

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
1:30 PM - 3:00 PM
•
$58
5 - 8 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
3:00 PM - 5:00 PM
•
Free
The Purple Pig
7:00 PM - 8:30 PM
•
$72
Hotel Blake, an Ascend Hotel Collection Member
Polished hotel in a 19th-century building offering airy rooms & suites, plus a cafe/bar & a gym.
7:30 AM - 7:30 AM
•
Free

Budget breakdown: $1977 In total

Activities & Food:$1887
Transport:$90