Chicago Explorer
See "The Bean" in person!
Spend 3, 4, or 5 nights in The Windy City! Explore Chicago's main sights, like Millennium Park, Buckingham Fountain, Navy Pier, and more. Try deep-dish pizza and a Chicago-style hot dog! There's nothing like Chicago, and it's time to discover its magic.Â
Book with confidence! Â
Our Flexible Change Plan is included with this package , allowing you to cancel and rebook at a later date for any reason (even COVID-19) up to 14 days before departure for a full credit that can be used for travel at a later date. See Terms & Conditions for more details.Â
What's Included
- Roundtrip economy class airfare into Chicago (ORD)
- 3 nights in Chicago at The Whitehall Hotel
Great Ways to Explore
Check out the Fulton Market District for hip eateries and a cool shopping scene.Â
Take a stroll along the Chicago Riverwalk!Â
See Wrigley Field and consider catching a Cubs game.Â
Walk from Millennium Park to Grant Park, and stop to see statues and fountains along the way.Â
Indulge in delicious deep dish pizza in River North!Â
Explore the charming streets of Chicago! From Millennium Park to Wrigley Field, there is tons to see and do in the "Windy City." Try your first deep-dish pizza at a classic restaurant, and take an obligatory photo in front of "The Bean!"Â
Check out the trendy Fulton Market District, filled with chic restaurants transformed from historic warehouses. Go shopping on the Magnificent Mile, then ride the Ferris wheel at Navy Pier. Visit Buckingham Fountain, then pass by the famous Chicago Theatre! Ready for fun? Chicago's waiting!Â
Please note that some package inclusions may be restricted or unavailable at time of travel. We will substitute them with similar options of equivalent value, as available.
Upgrade to Include Even More!
Add the following to your vacation:
- Skydeck Chicago Admission
- Classic Bites in River North Food Tour
- Roundtrip economy class airfare into Chicago (ORD)
- 3 nights in Chicago at The Whitehall Hotel
Check out the Fulton Market District for hip eateries and a cool shopping scene.Â
Take a stroll along the Chicago Riverwalk!Â
See Wrigley Field and consider catching a Cubs game.Â
Walk from Millennium Park to Grant Park, and stop to see statues and fountains along the way.Â
Indulge in delicious deep dish pizza in River North!Â
Explore the charming streets of Chicago! From Millennium Park to Wrigley Field, there is tons to see and do in the "Windy City." Try your first deep-dish pizza at a classic restaurant, and take an obligatory photo in front of "The Bean!"Â
Check out the trendy Fulton Market District, filled with chic restaurants transformed from historic warehouses. Go shopping on the Magnificent Mile, then ride the Ferris wheel at Navy Pier. Visit Buckingham Fountain, then pass by the famous Chicago Theatre! Ready for fun? Chicago's waiting!Â
Please note that some package inclusions may be restricted or unavailable at time of travel. We will substitute them with similar options of equivalent value, as available.
Add the following to your vacation:
- Skydeck Chicago Admission
- Classic Bites in River North Food Tour
Departure Airport:
Departure Month:
Prices From:
Day 1. Welcome to Chicago, Illinois!
Touch down in the "Windy City!" First thing's first: head to your hotel and check-in.
Spend the rest of your first day getting to know the city! Wander through Chicago and treat yourself to a delicious first-night meal.Â
Check-in - The Whitehall Hotel
Just a short walk from the shopping and dining of the Magnificent Mile, this stylish hotel boasts luxury, comfort, and convenience. Step into The Whitehall and feel immersed in an air of history and sophistication. Check-in with the friendly 24-hour reception team, then head up to your spacious room. Inside, you'll find free WiFi, luxurious bedding, marble bathrooms, and modern technology.Â
After you settle in, treat yourself to a drink from the bar, then a delicious meal at the upscale onsite restaurant. Too cozy to leave your bed? Just order room service!Â
Day 2. Chicago, Illinois
Consider a trip up to the 103rd floor of Willis Tower! Skydeck Chicago is a fantastic way to see stunning views of the city. Or, you may want to continue getting to know the city with a stroll along Chicago Riverwalk.Â
However you decide to spend the day, make the most of your first full day in Chicago!Â
Chicago Riverwalk
Day 3. Chicago, Illinois
A visit to Chicago isn't complete without a stop at Millennium Park! Take a photo in front of the famous "Bean" and enjoy the architecture and scenery that fills this special park.Â
Just south of Millennium, you'll find Grant Park and Buckingham Fountain. Commonly referred to as "Chicago's front yard," this 300+-acre green space starts at the eastern edge of the Loop and spans down to the Near South Side.Â
Thinking about dinner? Consider a delicious meal in the trendy West Loop/Fulton Market District area.
Millennium Park, Chicago
Day 4. Depart Illinois
It's time to wave goodbye to Chicago. Pack your bags and head to the airport for your flight home.Â