Discover the Best of Chicago: 8-Day Itinerary

Suany Tovares

18 Nov 2023

Embark on an unforgettable journey through the vibrant city of Chicago with this 8-day itinerary. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$844

$ 53

Selina Chicago

Depart from your stay 🏨

23 - 28 min

Directions

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

7:30 AM - 8:30 AM

•

$133

8 - 11 min

Directions

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

9:00 AM - 1:00 PM

•

$263

17 - 21 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.

1:30 PM - 3:00 PM

•

$252

12 - 17 min

Directions

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

3:00 PM - 4:00 PM

•

Free

12 - 17 min

Directions

Full-service restaurant.

12:30 PM - 2:00 PM

•

$196

Day 2

$602

$ 35

Selina Chicago

Depart from your stay 🏨

15 - 18 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

•

$161

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

•

Free

13 - 20 min

Directions

Full-service restaurant.

12:30 PM - 2:00 PM

•

$196

9 - 14 min

Directions

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

2:00 PM - 4:00 PM

•

Free

12 - 17 min

Directions

7:00 PM - 8:30 PM

•

$245

Day 3

$1180

$ 53

Selina Chicago

Depart from your stay 🏨

14 - 17 min

Directions

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

•

$147

12 - 17 min

Directions

State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.

9:00 AM - 12:00 PM

•

$350

13 - 16 min

Directions

Urban American tavern in Chicago's Block 37

12:30 PM - 2:00 PM

•

$224

4 - 5 min

Directions

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

2:00 PM - 4:00 PM

•

$263

4 - 5 min

Directions

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

•

$196

Day 4

$765

$ 53

Selina Chicago

Depart from your stay 🏨

11 - 14 min

Directions

7:30 AM - 8:30 AM

•

$154

4 - 5 min

Directions

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

9:00 AM - 10:00 AM

•

Free

4 - 5 min

Directions

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

10:30 AM - 11:30 AM

•

Free

11 - 14 min

Directions

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.

12:00 PM - 1:30 PM

•

$203

12 - 18 min

Directions

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

1:30 PM - 4:30 PM

•

$219

12 - 17 min

Directions

Polish/Italian. Pizza/pierogi Craft beer/polish vodkas

7:00 PM - 8:30 PM

•

$189

Day 5

$779

$ 35

Selina Chicago

Depart from your stay 🏨

10 - 12 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

•

$175

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

9 - 11 min

Directions

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

11:30 AM - 1:00 PM

•

$219

12 - 17 min

Directions

1:30 PM - 3:00 PM

•

$203

3 - 4 min

Directions

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

3:00 PM - 4:00 PM

•

Free

4 - 6 min

Directions

Shaw’s is two restaurants in one – a jazzy, sophisticated, seafood restaurant and a carefree, lively oyster bar. Both serve top-grade fish and shellfish, several varieties of just-shucked oysters, and inventive sushi and sashimi combinations, made with the freshest fish in town.

7:00 PM - 8:30 PM

•

$182

Day 6

$1421

$ 70

Selina Chicago

Depart from your stay 🏨

9 - 11 min

Directions

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

•

$126

10 - 15 min

Directions

Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.

9:00 AM - 11:00 AM

•

Free

17 - 21 min

Directions

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

11:30 AM - 2:30 PM

•

$924

6 - 9 min

Directions

Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago

3:00 PM - 4:30 PM

•

$182

5 - 6 min

Directions

7:00 PM - 8:30 PM

•

$189

Day 7

$602

$ 35

Selina Chicago

Depart from your stay 🏨

9 - 11 min

Directions

Fisk & Co blends the vibe of Belgium’s lively bistros with the spirit of Chicago’s historic restaurant industry.

7:30 AM - 8:30 AM

•

$147

6 - 9 min

Directions

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

9:00 AM - 11:00 AM

•

Free

10 - 15 min

Directions

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

11:30 AM - 1:30 PM

•

Free

5 - 8 min

Directions

2:00 PM - 3:30 PM

•

$203

4 - 5 min

Directions

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

3:30 PM - 4:30 PM

•

Free

3 - 4 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

•

$252

Day 8

$1087

$ 35

Selina Chicago

Depart from your stay 🏨

13 - 16 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

•

$175

4 - 5 min

Directions