Highland Holidays

Photo by Joe Farmer

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Top Flight + Hotel Deals in Highland

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 4 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
The property is very convenient, but the rooms are extremely small. Our toilet did not work took forever to flush if you’re on the high floors. Not really no views like they said.

Reviewed on 11 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 4 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 2 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Terrace 16 resto has the best view in Chicago outstanding service. Hotel is located right next to the river cruises. Walgreens is 3 minutes away by foot. Very safe neighborhood several excellent restaurants within 10 minutes on foot. Try Wildberry resta for breakfast excellent food. Sanda for Asian food and Grand Boucher French The pizza place next to hotel (bonjiourno) overrated and subpar

Reviewed on 12 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 4 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 4 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,927 reviews)
Great location, very convenient. Short walk to a lot of food options. The room furniture could use an update though. You’ll sink right into the bed and couch.

Reviewed on 11 Aug 2025

Top hotels in Highland

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 19 Aug to 20 Aug
€125
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"The staff at both check in and check out were so pleasant to deal with. They made us feel very welcome."

Reviewed on 11 Aug 2025

Hilton Chicago/Oak Lawn
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is €124 per night from 1 Sept to 2 Sept
€124
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
"Air Conditioner"

Reviewed on 11 Aug 2025

Ameristar Casino Hotel East Chicago
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €68 per night from 1 Sept to 2 Sept
€68
1 Sept - 2 Sept
includes taxes & fees
6.2/10 (64 reviews)
"Good"

Reviewed on 11 Aug 2025

Motel 6 - Chicago, IL
See all 845 properties in Highland
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 Highland holiday package cost?
Offering great value package deals from €1,102 on Expedia, you'll be surprised at how little a holiday to Highland costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Highland?
You can generally find lower rates and better availability in January, February and November. Explore our cheap Highland holiday packages and you could get some great off-season discounts.
How many days is enough for Highland?
With a well-planned schedule, you can easily hit the most popular Highland attractions in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Highland holiday for longer.
How to find the best Highland package deals?
Use Expedia's handy filters to help you find some unbeatable Highland 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 break for midweek, or search for Highland package deals in the low season. Play around with 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 as early as possible.
Is it cheaper to book a Highland holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and hotels individually. Better still, you can tailor your Highland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Highland?
If you're considering a spontaneous Highland trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Highland?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Highland.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the biggest expense during your trip to Highland.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to get to in Highland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalised Highland holiday package.

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