Highland Holidays from £1,354
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Your Highland Holiday
Spend less time travel planning and more time having exciting adventures with a Highland holiday package. The neighbourhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Centre are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland holiday is only a few clicks away with Expedia.
Top Highland Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was £1,868, price is now £1,354 per person
£1,354
per person
3 Aug - 8 Aug
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable
Reviewed on 26 May 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £3,557, price is now £2,423 per person
£2,423
per person
4 Jul - 11 Jul
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
This is a great option especially when traveling with family or a group. I loved having the extra space of a condo rather than hotel rooms. It’s in a great walkable location.
Reviewed on 25 May 2026
Level Chicago Fulton Market
Downtown Chicago
Price was £1,950, price is now £1,374 per person
£1,374
per person
2 Aug - 7 Aug
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on 22 May 2026
Level Chicago – Old Town
Downtown Chicago
Price was £2,219, price is now £1,640 per person
£1,640
per person
4 Jul - 11 Jul
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on 18 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £2,896, price is now £2,185 per person
£2,185
per person
4 Jul - 11 Jul
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast
Reviewed on 26 May 2026
Highland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Midway Intl. Airport (MDW) |
Population | 22,900 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Whihala Beach, Mascot Hall Of Fame and Lake Street Beach |
Top hotels in Highland
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is £102 per night from 3 Jun to 4 Jun
£102
3 Jun - 4 Jun
includes taxes & fees
8.6/10 Excellent! (1,061 reviews)
"Always a nice stay."
Reviewed on 23 May 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is £140 per night from 7 Jun to 8 Jun
£140
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (391 reviews)
"The hotel staff was amazing and the bartenders and staff at the Alto Restaurant on the rooftop were also fantastic! The only complaints I have are that the AC did not cool down as well as we would have liked. The lowest we could get it to was 70/71 and it was not comfortable for sleeping. Also, the ..."
Reviewed on 25 May 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is £138 per night from 27 May to 28 May
£138
27 May - 28 May
includes taxes & fees
6.8/10 (1,002 reviews)
"Nice staff, clean, nice spot. Definitely will stay here the next time I’m in Chicago"
Reviewed on 25 May 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
