Chicago Holiday Packages

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Chicago Holiday Packages

Chicago, Illinois, is the perfect choice for an American holiday—it has a busy, powerful vibe similar to New York, with just as much to do and see. Chicago packages are your ticket to an American Midwest secret: “The Windy City” has some of the best food, shopping and nightlife in the U.S.—at least, according to the locals! Why not decide for yourself on your next holiday?

Things to Do in Chicago

Navy Pier is a can’t-miss activity for any holiday in Chicago. The 45m-tall Ferris wheel is sure to catch your attention take a spin for great city views. Then do your best sailor swagger into the shops, where you just might find those perfect skyline-shaped chocolates. Don’t be “a-freud” to stop and chat with the statue of TV-psychologist Bob Newhart, whose couch is designed for therapeutic confessions (and photo ops). Hungry? Travel to the tropics inside Crystal Gardens, a one-acre greenhouse with palm trees, fountains and a variety of restaurants.

If you’re in the mood for some education, or the weather just isn’t on your side, explore indoors at one of Chicago’s museums. Always wanted to see the world from an ant’s perspective or learn about man-eating lions in Kenya? The Field Museum of Natural history, one of the largest in the world, is your playground. You could also book a Chicago car hire and head north to the Illinois Railway Museum or south to the Museum of Science and Industry.

Shopping, Dining & Nightlife

The money you’ve saved with our Chicago package deals is probably burning a hole in your pocket, so it’s time to decide: What’s your shopping style? The Magnificent Mile lives up to its name, with world-famous luxury brands and posh boutiques. In the Loop neighbourhood, rock collectors can find the perfect marquise cut on Jewelers Row, while bargain hunters can dig through discount racks on State Street. A Chicago holiday near Millennium Park is the perfect home base for shopaholic getaways, with both these neighbourhoods within walking distance.

You can show off your new diamonds at dinner without even leaving Mag Mile—it’s one of the best neighbourhoods for upscale dining. However, Chicago holidays are best spent exploring go northwest to find up-and-coming Lincoln Park, filled to the brim with the vanguard of experimental cuisine. Get your hands on mozzarella balloons, inside-out eggs benedict and crispy pig’s ears, and your taste buds will never be the same.

Swanky sightseers can keep their holiday going into the wee hours in Gold Coast, an area that is, you guessed it, on the Lake Michigan coast and very exclusive. Head over to stylish Rush Street to get your groove on with live jazz, reggae or funk. For the younger (or just hipper) crowd, Wicker Park is all about trendy cocktails, groovy tunes and a laid-back vibe. Plus, it’s got a subway stop on the 24-hour Blue Line, so you can easily get back downtown without even springing for a cab.

What’s Next?

The next steps are easy—listen to your holiday self and book your getaway with Wotif. We have the best Chicago hotel packages, because you can mix and match with flights to the same destination to create your perfect escape. Check us out today.

Top Chicago hotels

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$295 per night from 12 May to 13 May
NZ$295
per night
12 May - 13 May
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
"It's a nice hotel. Classic building so don't expect big rooms, and the elevator is over taxes so you might have to wait your turn. Still, location is excellent and staff are great. Good value that's for sure."

Reviewed on 8 May 2024

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$294 per night from 12 May to 13 May
NZ$294
per night
12 May - 13 May
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Chicago, May 2024
"Whenever we stay in Chicago, we always stay at the Congress Hotel and get a lakeview room. The Congress is not the most luxurious or fanciest but it has an old world charm you just don't find with new hotels. The room was nice and clean. The bed was not as comfortable as other rooms we have stayed ..."

Reviewed on 7 May 2024

Congress Plaza Hotel
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 27 May to 28 May
NZ$225
per night
27 May - 28 May
Book a stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
"A property that’s right in the heart of the magnificent mile. Easy walking distance to food options. Have stayed here multiple times. There’s a self park garage right next door, or for $10 more you can valet at the hotel."

Reviewed on 7 May 2024

Warwick Allerton - Chicago
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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.