Illinois Holiday Packages

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Get great package deals to Illinois's top cities

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Chicago

Chicago
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Rockford

Rockford
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Bloomington

Bloomington

Top Illinois holiday packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,505, price is now AU$2,382 per person
AU$2,382
per person
16 Oct - 21 Oct
found 11 hours ago
Return direct flight included
Montego Bay (MBJ) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$4,086, price is now AU$2,937 per person
AU$2,937
per person
16 Oct - 21 Oct
found 11 hours ago
Return direct flight included
Montego Bay (MBJ) to Chicago (ORD)
9.4/10 Exceptional! (3,839 reviews)
Great location, spacious and clean rooms, and accommodating staff. We would absolutely stay here again!

Reviewed on 16 Sept 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,376, price is now AU$2,459 per person
AU$2,459
per person
16 Oct - 21 Oct
found 11 hours ago
Return direct flight included
Montego Bay (MBJ) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
Staff was amazing! So many things to do and the view from the room was amazing.

Reviewed on 16 Sept 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was AU$3,240, price is now AU$2,393 per person
AU$2,393
per person
16 Oct - 21 Oct
found 11 hours ago
Return direct flight included
Montego Bay (MBJ) to Chicago (ORD)
9/10 Wonderful! (1,451 reviews)
TV was not working in both rooms I was in. Service was very slow, I had to remind the staff more than twice what I needed for the room

Reviewed on 16 Sept 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,296, price is now AU$2,511 per person
AU$2,511
per person
16 Oct - 21 Oct
found 11 hours ago
Return direct flight included
Montego Bay (MBJ) to Chicago (ORD)
9/10 Wonderful! (3,881 reviews)

Top Illinois hotels

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$298 per night from 13 Oct to 14 Oct
AU$298
13 Oct - 14 Oct
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast: Pet-friendly hotel with free WiFi and a bar/lounge. Located in a shopping district.
"I loved the location. The staff were very helpful and patient. The fact that you guys were located by the beach was Awesome. We will definately be back"

Reviewed on 16 Sept 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 20 Sept to 21 Sept
AU$265
20 Sept - 21 Sept
includes taxes & fees
River Hotel: Pet-friendly hotel with free WiFi and room service. Located in the city centre.
Opens in a new windowRiver 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 AU$291 per night from 27 Sept to 28 Sept
AU$291
27 Sept - 28 Sept
includes taxes & fees
Congress Plaza Hotel: Business-friendly hotel with free WiFi and 2 restaurants. Located in the city centre.
Opens in a new windowCongress Plaza Hotel
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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.

Your guide to epic deals and sweet holiday packages to Illinois

How much are holiday packages to Illinois?

You can book an awesome holiday in Illinois from just AU$2,382 on Wotif. Check our deal cards for details.

What’s included in Wotif’s Illinois holiday package deals?

Illinois packages can bundle everything: flight + hotel + car hire. But you can go for hotel + car hire without the flight. Or flight + hotel. You do you.

Can I cancel my Illinois holiday plans on Wotif?

Yes. Within 24 hours of booking, you can cancel and get your money back on many of our packages. After 24 hours, your airline or hotel may charge a fee. Check your itinerary or our Customer Service Portal to know more.

How do I find the best holiday package to Illinois?

Just take a look through all our terrific offers or select your dream spot in Illinois, and we’ll serve up some delicious Illinois holiday deals that’ll make you swoon and save you cash.

How do I get the best holiday deals to Illinois?

We have stacks of ready-made holidays and luxury getaways in Illinois, and usually the more flexible you can be on dates, the better the deal. Simply enter your travel details and we’ll find you loads of wallet-friendly deals. You can filter by trip length, hotel stars and flight class and – ta-daa – best break ever. Added bonus: our Price Promise refunds the difference if you find a lower price up to 24 hours before check-in.

When is the best time to visit Illinois?

usually has the best bargain breaks when hotel prices are often cheaper, and Illinois is quieter. But for more of a buzz, plan your visit in .

Why choose Wotif to book your holiday package to Illinois?

Plan your trip to Illinois today and you could save 32 on your next escape and pay just AU$1,149. With Wotif, you know you’ve got great flexibility and those awesome Mates Rates deals, too.

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