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The Windy City!

Chicago Explorer

From * Per Person
3+ Nights
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Limited Time Special Offer
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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. 

Book with confidence!  
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. 

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. 

  • Take a stroll along the Chicago Riverwalk! 

  • See Wrigley Field and consider catching a Cubs game. 

  • Walk from Millennium Park to Grant Park, and stop to see statues and fountains along the way. 

  • Indulge in delicious deep dish pizza in River North! 

Package Overview

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!" 

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! 

Show Detailed Itinerary

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 & Include Even More!

Add the following to your vacation:

  • Skydeck Chicago Admission
  • Classic Bites in River North Food Tour
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Package ID: PK-GC4P-SH-CE-ORD

Please note that some elements called out in the following suggested itinerary may not be included in your package. Check "What's Included" above for full details on inclusions. As we all go through the recovery together, the fluid nature of this event means some venues and attractions may have restrictions or closures. Please check online resources close to the time of travel to better plan your own day-to-day itinerary.

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. 

Check-in - The Whitehall Hotel

Chicago, Illinois, United States
4 out of 5 stars

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. 

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! 

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. 

However you decide to spend the day, make the most of your first full day in Chicago! 

Chicago Riverwalk

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. 

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. 

Thinking about dinner? Consider a delicious meal in the trendy West Loop/Fulton Market District area.

Millennium Park, Chicago

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. 

Fly home!

Advertised package rates are based on select departures as noted on the booking calendar above, were available via the Great Value Vacations website and may not represent current prices.

Vacation packages include round-trip economy class airfare on valid international carriers as noted in specific package inclusions and as indicated on booking engine calendar, which may also include code share flight agreements between carriers as indicated during the booking process. Carriers may vary based on city of origin.

Air fares are based on a 14-day advance purchase and include round-trip economy class airfare, including carrier and government-imposed taxes and fees, and the September 11th Security Fee of $5.60 per enplanement originating at a U.S. airport. Fluctuations in exchange rates may affect some taxes or fees. Other departure dates and origins are available at slightly higher rates. Fares apply to North American originating passengers only, and are not eligible for accrual of frequent flyer points/mileage. Seats are limited and fares may not be available on all flights. Child/infant discounts are not available, and stopovers are not permitted. Advance seat selection is controlled by the carrier(s), and may not be available on all flights. Baggage fees may apply; please check with carrier for specific policies.

Vacation packages are subject to availability, are capacity controlled, may not be available on every date or on all flights, and may be restricted to certain hotel room and car categories. Higher rates may also be available throughout travel period. Full payment is required at the time of reservation. Rates cannot be combined with any other discount/promotion, and are valid for new bookings only. Offers may be changed or withdrawn at any time without notice. Website contains special pricing that is exclusively for Internet sale only. Bookings made through our call center may incur a concierge fee of up to $25 per person.

Escorted vacation packages are per person based on two travelers (unless otherwise specified), and typically include hotel accommodations; transportation with professional driver/guide; sightseeing as listed, some meals, local taxes, hotel service charges and porterage of one (1) suitcase per person, due to limited capacity on motor coaches. Space is limited and prices may be restricted to certain travel dates, length of stay or room type. Driver and guide gratuities are not included, and are at the discretion of the traveler. Terms and conditions apply. Minimum child ages and handicapped traveler restrictions may apply on escorted tours; please call for details.

Promo Code Offer Details: All promotions are subject to availability, valid for new bookings only, cannot be combined with any other promotion, discount, voucher or any other offers, and are not redeemable for cash. Offers are available for phone bookings via our reservation agents as well as online. This promo code can be input online on the payment screen. The call center is open Monday through Friday 9AM – 9PM ET, Saturdays 10AM – 6PM ET. Discounts will apply only once per passenger and are not valid for airfare only, or any other products or services. If a flight reservation is changed or cancelled, the original fare basis rules apply (plus any increase in fare). Additional restrictions may apply.

Call 1-800-896-4600 or go to https://www.greatvaluevacations.com/travel/terms-and-conditionsfor full details on change/cancellation policy. 
Chicago, Illinois, United States

The Whitehall Hotel

Upscale comfort near the Magnificent Mile

The Whitehall Hotel Start over On a full map

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