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Chicago Itinerary

Famous for world-renowned museums, jaw-dropping waterfronts, ground-breaking music, award-winning theatrical productions, with over 300 parks and countless iconic buildings, Chicago is worth visiting all year round!

01:00 am

Arrive

Flight Arrives in Chicago

01:30 am

Check-in

at Freehand

02:00 am

Sleep

07:00 am

Breakfast

Breakfast at Hotel

09:00 am

Willis Tower

Chicago

The Willis Tower is a 108-story, 1,450-foot skyscraper in Chicago. The tower has 108 stories as counted by standard methods, though the building’s owners count the main roof as 109 and the mechanical penthouse roof as 110.

Location:
233 S Wacker Dr, Chicago, IL 60606, United States

10:00 am

Shedd Aquarium

Shedd Aquarium

Chicago

Shedd Aquarium is an indoor public aquarium in Chicago, Illinois, in the United States. Opened on May 30, 1930, the 5 million US gal aquarium was for some time the largest indoor facility in the world. Today it holds about 32,000 animals.

Location:
1200 S DuSable Lake Shore Dr, Chicago, IL 60605, United States

11:00 am

Field Museum

Chicago

The Field Museum of Natural History, also known as The Field Museum, is a natural history museum in Chicago, Illinois, and is one of the largest such museums in the world.

Location:
1400 S Lake Shore Dr, Chicago, IL 60605, United States

12:00 pm

Lunch

Explore local eateries

14:30 pm

Chicago Architecture River Cruise

Chicago

Watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Location:
401 N Michigan Ave, Chicago, IL 60611, USA

18:00 pm

Andersonville Pub Tour

Chicago

Get a “taste” of Andersonville—a historically landmarked neighborhood settled by Swedish farmers in the 1850s. See the culture reflected in the classic architecture and thriving establishments as we drop into colorful local pubs for vast selections of local brews.

Location:
Hamburger Mary’s, 5400 N. Clark St

07:00 am

Breakfast

Breakfast at Hotel

09:00 am

Pedway Tour

Pedway Underground Winter Tour

Chicago

Stay inside and warm on the Chicago Pedway Tour, discover the fascinating “city below the city” used by Chicagoans every day—the Pedway. From the State of Illinois Building to the Cultural Center, this walking tour introduces guests to the history and surprises of the Pedway which connects over 50 buildings and 40 city blocks.

Location:
100 W Randolph St, Chicago, IL 60601

11:00 am

Chicago Riverwalk & North Loop Walking Tour

Riverwalk & North Loop Tour

Chicago

Enjoy the perfect mix of Chicago history, architecture and beautiful views along the Chicago Riverwalk. This Chicago Walking tour has something for everyone making this one of the most popular tours.

Location:
99 Chicago Riverwalk on the northwest corner of Michigan Avenue and Wacker Drive

13:00 pm

Lunch

at Portillo’s Hot Dogs 

14:00 pm

Millennium Park & Michigan Ave

Walking Tour

Chicago

Get ready to check a lot off your Chicago bucket list! Guests on our Millennium Park and Michigan Avenue tour cross the Chicago River, experience Cloud Gate and will see Buckingham Fountain up close and personal.

15:30 pm

Garfield Park Conservatory_

Garfield Park Conservatory

Chicago

Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between.

Location:
300 N Central Park Ave, Chicago, IL 60624, United States

18:00 pm

Dinner

Explore local eateries

19:00 pm

Rest

Rest and freshen up at Hotel

22:00 pm

Primary Night Club

Primary Night Club

Chicago

Local & international DJs spin house & EDM at this intimate dance club with a wall of LED lights.

Location:
5 W Division St, Chicago, IL 60610, United States

07:30 am

Breakfast

Breakfast at Hotel

11:00 am

Chicago Pizza Tours

Chicago Pizza Tours

Chicago

Chicago Pizza Tours are a fun and informative way to explore the city’s most famous culinary export. The tours adapted in 2020 to include a bit of a luxury upgrade. The Quarantine Pizza Tour features everything you love and expect from a food-focused adventure—with the addition of a limousine escort from where you’re staying.

15:00 pm

Lincoln Park Zoo

Lincoln Park Zoo

Chicago

Offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits.

Location:
2001 N Clark St, Chicago, IL 60614, United States

17:30 pm

Humboldt Park

Humboldt Park

Chicago

One of Chicago’s prettiest parks, this 207-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt).

19:00 pm

Cindy's Rooftop

Chicago

Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.

Location:
12 S Michigan Ave, Chicago, IL 60603, United States

20:15 pm

The Escape Game Chicago

The Escape Game

Chicago

Follow clues and solve puzzles to complete your mission together. You might escape…You WILL have fun! Choose to play one of five uniquely immersive games: Gold Rush, Prison Break, Special Ops, The Heist, and Mission: Mars!

Location:
42 E Ontario St, Chicago, IL 60611, USA

21:15 pm

Three Dots and A Dash

Three Dots And A Dash

Chicago

Chicago’s premier tropical bar and craft cocktail destination hidden below the bustling streets of River North. The secret hideaway – named one of The World’s 50 Best Bars by Drinks International – is led by cocktail expert Kevin Beary. 

Location:
435 N Clark St, Chicago, IL 60654, United States

07:00 am

Breakfast

Breakfast at Hotel

10:00 am

Urban Kayaks Paddleboarding

Urban Kayaks Paddleboarding

Chicago

Move through the pulsing heart of the city on the river or travel Lake Michigan and circle Museum Campus (featuring the Field Museum, Adler Planetarium, Shedd Aquarium and Soldier Field). 

Location:
Monroe Harbor

12:00 pm

Lunch

at Little Goat Diner

13:00 pm

Chicago Sporting Events

NFL Live (Chicago Bears)

Soldier Field, Chicago

Watch this professional American football team based in Chicago. The Bears compete in the National Football League as a member club of the league’s National Football Conference North division.

You can also check other sporting events of Chicago in our curated idea board!

Location:
Soldier Field Stadium, Chicago, IL, United States

17:00 pm

Check out

from Freehand Hotel

21:00 pm

Departs

Flight departs from Chicago

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Adventure (32)

Outdoors (12)

Romantic (47)

Family (76)

Relaxing (64)

Weekend (31)

Foodies (14)

Cultural (72)

Hike, Dive, Eat, Sunbath.
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