Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Chicago Riverwalk
9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Michigan Avenue
9.4/10 (15,813 reviews)
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Grant Park
9.2/10 (12,844 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All-inclusive Central Chicago holidays: everything you need to know
Can I book Central Chicago all-inclusive holidays with airfare and meals?
Use the all-inclusive filter to find amazing all-inclusive package holidays to Central Chicago, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.
Why should I book a Central Chicago adults-only all-inclusive holiday?
If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Central Chicago and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.
Can I book last minute all-inclusive holidays to Central Chicago?
Last-minute breaks are a great way to find very cheap all-inclusive holidays to Central Chicago. If you can be flexible with your holiday dates, browse our best Central Chicago deals and use the all-inclusive filter to add everything that makes your hols perfect.
Can I book a cheap all-inclusive Central Chicago trip?
There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Central Chicago. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.
What should I look for when booking a 5-star all-inclusive holiday to Central Chicago?
All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.
What should I consider when booking a Central Chicago all-inclusive family holiday?
If you’re holidaying with tots in tow, book an all-inclusive Central Chicago package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.
How can I find the best deals on all-inclusive holidays to Central Chicago in 2026/2027?
There are great all-inclusive deals galore in Central Chicago. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.
Can I book an all-inclusive Central Chicago package with free cancellation and/or flexible dates?
Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.
Why should I book an all-inclusive Central Chicago package holiday with Expedia?
With a huge range of all-inclusive Central Chicago trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.