East Chicago Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in East Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (8,981 reviews)
"I love it"

Reviewed on 5 Aug, 2025

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$294 per night from 23 Aug to 24 Aug
S$294
23 Aug - 24 Aug
includes taxes & fees
8.2/10 Very Good! (1,829 reviews)
"Overall, staff was super friendly and helpful. Was able to check-in 2 hours early. The hotel itself is older and a little dated so the shower and toilet were working but could use an upgrade. However the room was clean and beds were comfortable. Super convenient and so many places nearby- walking ..."

Reviewed on 4 Aug, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is S$221 per night from 24 Aug to 25 Aug
S$221
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,334 reviews)
"Thanks beautiful place"

Reviewed on 3 Aug, 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,176 properties in East Chicago
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.

What to do in East Chicago

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

S$178
per adult
78% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 Chicago
See all activities in East Chicago

Frequently asked questions

How much does an East Chicago holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. But how much your holiday to East Chicago costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to East Chicago?
You can usually find lower prices and better availability in November, December and January. Take a look at our cheap East Chicago holiday packages and you could get some great off-season deals.
How many days is enough for East Chicago?
Typically, a handful of days is enough to explore the main attractions during your East Chicago holiday. However, if you'd like to have more time to unwind or go on day trips, consider extending your trip.
How to find the best East Chicago package deals?
Use Expedia's handy filters to help you find some great East Chicago package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for East Chicago package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.
Is it cheaper to book an East Chicago holiday as a package?
You can enjoy significant savings on your next East Chicago getaway by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to East Chicago?
If you're considering an impromptu East Chicago getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to East Chicago?

  1. Choose your dates: What you want to do in East Chicago and your preferred season can help you decide when to travel.
  2. Set your budget: Consider costs such as food, flights and transportation when working out how much to set aside for your trip to East Chicago. Then, choose a hotel that fits your budget, whether that's a wallet-friendly stay or a more luxurious retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in East Chicago. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the ideal East Chicago holiday package for you.

* 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.