Chicago Heights Holidays

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Top Flight + Hotel Deals in Chicago Heights

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 17 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 17 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 17 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 17 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 17 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

Top hotels in Chicago Heights

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is €125 per night from 16 Sept to 17 Sept
€125
16 Sept - 17 Sept
includes taxes & fees
8.2/10 Very Good! (1,028 reviews)
"Bathroom was too small."

Reviewed on 26 Aug 2025

Hilton Chicago/Oak Lawn
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €135 per night from 4 Sept to 5 Sept
€135
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,174 reviews)
"Grate food, quite and clean"

Reviewed on 27 Aug 2025

Hampton Inn by Hilton Chicago-Midway Airport
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
Fully refundableReserve now, pay when you stay
The price is €43 per night from 2 Sept to 3 Sept
€43
2 Sept - 3 Sept
includes taxes & fees
6.8/10 (1,209 reviews)
"Friendly staff"

Reviewed on 27 Aug 2025

Motel 6 Bridgeview, IL
See all 786 properties in Chicago Heights
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.

Frequently asked questions

How much does a Chicago Heights holiday package cost?
Offering excellent value package deals from €723 on Expedia, you'll be surprised at how little a holiday to Chicago Heights costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chicago Heights?
You can generally find reduced prices and better availability in January, February and November. Browse our cheap Chicago Heights holiday packages and you could land some great off-season discounts.
How many days is enough for Chicago Heights?
The ideal duration of your Chicago Heights holiday depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to check out all the major sights and discover some hidden gems along the way.
How to find the best Chicago Heights package deals?
Begin your search for a Chicago Heights package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Chicago Heights package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chicago Heights adventure underway.
Is it cheaper to book a Chicago Heights holiday as a package?
You can enjoy significant savings on your next Chicago Heights retreat by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to browse some great 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 score a better deal.
When to book a holiday package to Chicago Heights?
If you're planning an impromptu Chicago Heights adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Chicago Heights?

  1. Pick your dates: The things you want to do in Chicago Heights and your favourite season can help you decide when to travel.
  2. Set a budget: Consider costs like transportation, flights and meals when working out how much to put aside for your trip to Chicago Heights. Then, choose a property that suits your budget, whether that's an affordable stay or a lavish getaway.
  3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Chicago Heights. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chicago Heights holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.