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Discover the Best of Chicago in 10 Days

Lorin Hamilton

Lorin Hamilton

7 Nov 2023

Embark on an unforgettable journey through the vibrant city of Chicago. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Day 1
+

$256

·

$ 10

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

12 - 15 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
8:00 AM - 10:00 AM
•
Free
6 - 9 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
1:00 PM - 2:30 PM
•
$144
7 - 10 min

~

Directions

The Purple Pig
7:00 PM - 8:30 PM
•
$112
Day 2
+

$236

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

12 - 15 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
8:00 AM - 10:00 AM
•
Free
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
•
$112
6 - 9 min

~

Directions

Cherry Circle Room
7:00 PM - 8:30 PM
•
$124
Day 3
+

$232

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

9 - 14 min

~

Directions

City Gallery in the Historic Water Tower
Chicago-focused gallery, specializing in photos, inside a 19th-century Gothic limestone landmark.
8:00 AM - 9:00 AM
•
Free
10 - 12 min

~

Directions

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
9:30 AM - 10:30 AM
•
Free
3 - 4 min

~

Directions

Mon Ami Gabi
1:00 PM - 2:30 PM
•
$128
6 - 9 min

~

Directions

Chicago Pizza & Oven Grinder
1:00 PM - 2:30 PM
•
$104
Day 4
+

$349

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

10 - 12 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
•
$125
8 - 11 min

~

Directions

Garrett Popcorn Shops
1:00 PM - 2:30 PM
•
$116
8 - 11 min

~

Directions

The Dearborn
Urban American tavern in Chicago's Block 37
7:00 PM - 8:30 PM
•
$108
Day 5
+

$345

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

15 - 18 min

~

Directions

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
8:00 AM - 11:00 AM
•
$125
9 - 14 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
1:00 PM - 2:30 PM
•
$116
7 - 10 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.
7:00 PM - 8:30 PM
•
$104
Day 6
+

$212

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

9 - 11 min

~

Directions

North Avenue Beach
8:00 AM - 10:00 AM
•
Free
16 - 23 min

~

Directions

Chicago Pizza & Oven Grinder
1:00 PM - 2:30 PM
•
$104
11 - 16 min

~

Directions

Twin Anchors Restaurant & Tavern
7:00 PM - 8:30 PM
•
$108
Day 7
+

$260

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

20 - 24 min

~

Directions

National Museum of Puerto Rican Arts & Culture
8:00 AM - 9:30 AM
•
Free
8 - 11 min

~

Directions

Flying Saucer
1:00 PM - 2:30 PM
•
$116
4 - 6 min

~

Directions

Rootstock Wine & Beer Bar
7:00 PM - 8:30 PM
•
$144
Day 8
+

$396

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

12 - 15 min

~

Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
8:00 AM - 11:00 AM
•
$128
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
•
$144
2 - 3 min

~

Directions

Cherry Circle Room
7:00 PM - 8:30 PM
•
$124
Day 9
+

$248

·

$ 20

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

20 - 24 min

~

Directions

Swedish American Museum
Celebrating Nordic culture & history with various programs including exhibits, tours & a kids' area.
8:00 AM - 9:30 AM
•
Free
3 - 4 min

~

Directions

Lady Gregory's
Lady Gregory’s is a Irish Gastro Pub serving a delicious menu and proudly boasting over 300 whiskeys! Come take a seat with Lady Gregory!
1:00 PM - 2:30 PM
•
$124
3 - 4 min

~

Directions

Calo Ristorante
Calo Ristorante offers the best in authentic Italian and American dishes. The dining room features naturally exposed brick walls and hardwood floors, with murals of Old World Italy for a traditional feel.
7:00 PM - 8:30 PM
•
$124
Day 10
+

$800

·

$ 30

Home2 Suites by Hilton Chicago River North

Depart from your stay 🏨

18 - 22 min

~

Directions

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
8:00 AM - 11:00 AM
•
$528
6 - 9 min

~

Directions

PR Italian Bistro
Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago
1:00 PM - 2:30 PM
•
$132
5 - 6 min

~

Directions

The Chicago Diner, Lakeview
7:00 PM - 8:30 PM
•
$140

Budget breakdown: $3534 In total

Activities & Food:$3334
Transport:$200