Cheap Vacations in Highland Park

Choose two or more items and save on your trip:

3-night Highland Park vacations

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North
Level Chicago – Old Town
Hotel Riu Plaza Chicago
Hyatt Regency McCormick Place Chicago
21c Museum Hotel Chicago
Park Hyatt Chicago
Embassy Suites by Hilton Chicago Downtown River North
The Royal Sonesta Chicago River North
Ambassador Chicago, part of JdV by Hyatt
Waldorf Astoria Chicago
Swissotel - Chicago
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4-night Highland Park vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Pendry Chicago
Hilton Chicago
Aloft Chicago Downtown River North
Arlo Chicago
Virgin Hotels Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown South Loop
The Emily Hotel
Fairmont Chicago at Millennium Park
Embassy Suites by Hilton Chicago Downtown River North
L7 Chicago by LOTTE

5-night Highland Park vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hilton Chicago
W Chicago - Lakeshore
Aloft Chicago Downtown River North
Congress Plaza Hotel
LondonHouse Chicago, Curio Collection by Hilton
Arlo Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown South Loop
Silversmith Hotel Chicago Downtown
Holiday Inn Express Hotel & Suites Chicago-Midway Airport, an IHG Hotel

6-7 night Highland Park vacations

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Hilton Chicago
Hotel Riu Plaza Chicago
The Emily Hotel
Congress Plaza Hotel
Aloft Chicago Downtown River North
Virgin Hotels Chicago
DoubleTree by Hilton Chicago - North Shore Conference Center
Palmer House a Hilton Hotel
W Chicago - Lakeshore
Hyatt Regency O'Hare Chicago
Hotel Felix River North/Magnificent Mile

Where is Highland Park?

Dying to visit Highland Park? Snap up that inexpensive flight already and start looking forward to your next cheap and chic escape!

It's a neighborhood in the well-loved city of Chicago. You'll find it sitting 22 miles to the north-west of the downtown area.

Last time they counted, the population of Chicago was 2,695,600.

Cheap Things to do in Highland Park

If the idea of costly ticket prices and entry fees sends a cold shiver down your spine, don't worry — we've got you covered! These free experiences in or near Highland Park will help you make the most out of your time and your budget:

  • Take a step back in time and visit the Trinity International University. This long standing attraction is an excellent place to get your fix of local history without having to pay for admission fees.
  • Want some time out from pounding the pavement? Head towards Rosewood Beach, kick off your boots and drink in the stunning views.
  • Stroll through perfectly kept grounds and unique plant displays at the Emily Oaks Nature Center, the River Trail Nature Center, Gallery Park and North School Park. There's nothing quite like whiling away an afternoon with Mother Nature, especially when it doesn't cost a penny!

Cheap Highland Park Vacation Package Deals

CheapTickets is not your average budget travel company. We're dedicated to helping you fulfill your affordable travel dreams. And remember, we refuse to make compromises on the quality of your experiences, accommodations or flights.

We have 500 partner airlines and no less than 500,000 properties internationally, so don't panic — we know where to scope out the best deals. You'll also be able to save up to $287 when you combine your bookings on flights and accommodations.

Relax knowing if you secure a package now and find a better price within 48 hours, we'll meet it and pay back the difference with our Price Guarantee. CheapTickets can fulfil your travel dreams at a price that won't hurt your hip pocket.

Get CheapCash

What could be more satisfying than pocketing the cheapest deal around? A cheap deal with rewards! With our rewards program, you'll be able to save cash on your next eligible CheapTickets hotel just by booking flights.

Super-thrifty savings on all eligible bookings — check! Bonus offers and perks as far as the eye can see — check! All you've got to do is log in to your account or sign up for free, join CheapCash and experience the benefits!

Cheap Car Rentals in Highland Park

Hi there, fellow cheapskate. We know you're eager to get the most out of your getaway for the tiniest amount of cash, so why not suss out renting a car while you're in Highland Park? It's a top way to save on expensive taxis if you're planning to move around a lot.

Cheap Hotels in Highland Park

You won't be able to base yourself in the middle of Highland Park, but you will be able to lay your head a little further out. Choose from 20 hotels just a short commute away.

Snap up a good deal at the Courtyard by Marriott Chicago Highland Park/Northbrook and the Residence Inn By Marriott Chicago Deerfield, our top accommodation picks. You'll find them at 1505 Lake Cook Road, Highland Park 60035, IL and 530 Lake Cook Rd, Deerfield 60015, IL respectively.

Flight deals to Highland Park

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Highland Park vacation

Don't see what you're looking for?
See all available properties in Highland Park
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.