Luxury holidays to Chicago
If you like your getaways to have VIP style, take a look at our luxury holidays to Chicago.
Extra special
If you’re in the market for a break with plenty of 5-star appeal, look no further – we’ve got loads of luxury holidays to Chicago to choose from.
Top-class hotels
We’ve cherry-picked the very best when it comes to hotels. These places pack in glossy interiors, pools that look like they’ve been plucked from a postcard, and top-of-the-range spas.
Fine dining
And when it comes to dining, these hotels lay on elegant restaurants with top-notch à la carte menus, as well as buffet spreads that you can enjoy on al fresco terraces. But you don’t have to eat in the hotel – there are plenty of upmarket eateries in the area, too.
That’s another great thing about our luxury holidays to Chicago – the flexibility. If you prefer to eat out, you can opt for a bed and breakfast, or self-catering deal. On the other hand, if you want to make the most of the hotel’s dining venues, go for a half board or All Inclusive deal.
More information
Find out more about what to expect on luxury holidays to Chicago by having a look through our online guide. It’s got lots of helpful tips and advice on where to go and what to do here.
Find Luxury Holidays in Chicago
Waldorf Astoria Chicago
in Chicago, United States of America
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TUI experiences
TUI experiences help you get more out of your holiday. And we've got thousands of experiences worldwide.
![Wendella’s 90 minute Chicago River architecture tour]()
Wendella’s 90 minute Chicago River architecture tour
16 ReviewsEnjoy a 90-minute comprehensive boat cruise of Chicago's legendary architectural wonders from the best seat in the house, the river.
![45-Minute Chicago Architecture River Cruise]()
45-Minute Chicago Architecture River Cruise
4 ReviewsDiscover Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.
Duration: up to 1 hour![360 Chicago Observation Deck Tickets]()
Entrance Tickets
360 Chicago Observation Deck Tickets
9 ReviewsAdmire Chicago from the 94th floor. Learn about Chicago's history and architecture and discover the CloudWalk and the 3D mural by Nate Baranowski.
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