Hinsdale Holidays

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Hinsdale Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was S$774, price is now S$592 per person
S$592
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I love the pool and exercise room access, breakfast was amazing

Reviewed on 1 Jul, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$978, price is now S$671 per person
S$671
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.

Reviewed on 2 Jul, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,006, price is now S$696 per person
S$696
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on 26 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,352, price is now S$983 per person
S$983
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The shower temp was about on the hot side no matter how low you had it. The bed& room were overall great

Reviewed on 3 Jul, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was S$824, price is now S$624 per person
S$624
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,941 reviews)
Very charming hotel. Loved the art deco bathroom! The room was large for an old inner city hotel. Plus you cannot beat the location!! So reasonably priced too. Definitely would stay again.

Reviewed on 1 Jul, 2026

Top hotels in Hinsdale

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 S$187 per night from 6 Jul to 7 Jul
S$187
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on 2 Jul, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 5 Jul to 6 Jul
S$278
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,834 reviews)
"We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay."

Reviewed on 2 Jul, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$306 per night from 5 Jul to 6 Jul
S$306
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,483 reviews)
"A lot of it was good, the rooms were very good. The AC was very good and the view from the bedroom. The only things I want to complain about is the expensive stuff and the TV in the bedroom not working/turning on. It costs a lot of money for car parking. The beds were one of the most comfortable ..."

Reviewed on 3 Jul, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,920 properties in Hinsdale
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.

Stay near popular Hinsdale attractions

Graue Mill and Museum

8.4/10 (94 reviews)
This historic waterwheel gristmill served as an Underground Railway station while grinding grain in the 1800s. Visitors can watch live milling demonstrations and explore interactive exhibits on 19th-century crafts.
See properties

What to do in Hinsdale

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Hinsdale

Frequently asked questions

How much does a Hinsdale holiday package cost?
Offering great value package deals from S$592 on Expedia, you'll be thrilled with how little a holiday to Hinsdale costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Hinsdale?
You're likely to find lower prices and greater availability in January, February and November. Check out our cheap Hinsdale holiday packages and you could get some great off-season discounts.
How many days is enough for Hinsdale?
The ideal duration of your Hinsdale holiday depends on what you'd like to see. Generally, a few days to a week will give you enough time to check out all the major sights and explore some hidden treasures along the way.
How to find the best Hinsdale package deals?
Use Expedia's handy filters to find some unbeatable Hinsdale package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Hinsdale package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Hinsdale holiday as a package?
You can enjoy significant savings on your next Hinsdale retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Hinsdale?
If you have your Hinsdale holiday dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Hinsdale?

  1. Choose when to get away: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to holiday in Hinsdale.
  2. Plan your budget wisely: On top of the price of your hotel, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Hinsdale.
  3. Decide how long to go for: Now that you're up to speed on Hinsdale, you can work out the ideal length of your break. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customised Hinsdale holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.