COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Cheap Vacations in Chicago

Choose one or more items to build your trip:

Chicago vacations

Residence Inn Chicago Downtown/Loop
Hotel Lincoln, part of JdV by Hyatt
Chicago Marriott Downtown Magnificent Mile
InterContinental Chicago Magnificent Mile, an IHG Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
The Drake
Hotel Essex Chicago
Holiday Inn Express & Suites Chicago O'Hare Airport, an IHG Hotel
Courtyard by Marriott Chicago Downtown River North
Hilton Chicago

3-night Chicago vacations

The Peninsula Chicago
Residence Inn Chicago Downtown/Loop
Freehand Chicago
Hotel Lincoln, part of JdV by Hyatt
The Westin Chicago Northwest
The Langham, Chicago
Fairmont Chicago at Millennium Park
Marriott Chicago Schaumburg
InterContinental Chicago Magnificent Mile, an IHG Hotel
The Westin Chicago River North
DoubleTree by Hilton Chicago - Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile

4-night Chicago vacations

Residence Inn Chicago Downtown/Loop
The Godfrey Hotel Chicago
Hotel Lincoln, part of JdV by Hyatt
The Peninsula Chicago
Freehand Chicago
The Westin Chicago Northwest
Best Western Grant Park Hotel
LEVEL Chicago – Old Town
DoubleTree by Hilton Chicago - Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
Fairmont Chicago at Millennium Park
Hotel Essex Chicago

Chicago Vacation Deal FAQ's

Where to find Chicago package deals?

On CheapTickets, you can find package deals in Chicago as low as $363!

When is peak season in Chicago?

July, June, May are very popular times to visit Chicago.

When is the best time to visit Chicago?

If you're looking for cheap vacations to Chicago, January is the best time to visit Chicago.

When is the worst time time to visit Chicago?

Prices for Chicago vacations can peak during October.

When is low season in Chicago?

We have found October, December, November to be the least-crowded time of the year to visit Chicago.

Where is Chicago?

Dirt-cheap plane tickets booked? Check. Affordable-yet-chic hotel sorted out? You know it. It's time to make your cheap vacation dreams a reality in Chicago!

It sits 19 miles to the north-west of East Chicago, and 597 miles north-west of Washington, the national capital.

It won't be too tricky to make new acquaintances in this part of Cook County. It boasts a population of some 2,695,600 locals.

Cheap Things to do in Chicago

Often, the most fabulous experiences are the cheapest. Get a real slice of local life with our suggestions for free things to see and do in or near Chicago:

  • Thrifty museum buffs will have a ball here. With attractions like the Driehaus Museum, the Fine Arts Building, the National Museum of Mexican Art and the Money Museum requesting no entry fees, you can wander down the halls, examine the exhibits and learn a thing or two without spending a dollar!
  • Attending arts and cultural events is an excellent way to get a feel for the character of the local area. Check out the programs at the Cloud Gate, the Museum of Contemporary Photography, the Crown Fountain and the ArchiTech Gallery to discover their free or cheap shows.
  • If you're hankering for some fresh air and outdoor experiences, you won't go wrong with Northerly Island Park. There's no charge to get in, so you might as well spend what you save on a round of drinks later on!
  • Want to discover a few things about the region's story? Can't stand forking out for entrance fees? Check out the University of Illinois Chicago, the Merchandise Mart, the Buckingham Fountain and Tribune Tower and get a free and intriguing history lesson!

Cheap Chicago Vacation Package Deals

When you book your getaway with CheapTickets, you can sit back and relax knowing that we'll handle all the hard work. We'll search out the lowest prices, and we'll never compromise on quality and comfort.

We have about 500 partner airlines and no less than 500,000 worldwide properties, so don't worry — you can bet your bottom dollar we'll find the thriftiest deals. You can also save as much as $290^ when you package your bookings on hotels and flights.

Let your inner penny-pincher breathe easy with our Price Guarantee. This is how it works — if within 48 hours you find your vacation deal for a better rate, we'll match it and refund you the difference. How's that for cheaptastic?

Get CheapCash

The best bargains and worthwhile rewards — it doesn't get easier on the wallet than that, does it cheapster? Just book your flight with us and you'll save heaps on your next qualifying CheapTickets hotel booking.

Taking advantage of the CheapCash rewards program couldn't be simpler. Sign up for a new account (for free!) or log in to your existing one, and you'll be able to save on eligible bookings, as well as getting intel on other amazing bonus offers and super-scrimpy perks!

Cheap Car Rentals in Chicago

Listen up, cheapster. Here's a suggestion that will make your escape not only economical, but a lot more comfortable. To save having to lift your luggage on and off buses or trains during your Chicago stay, why not look at a car rental? There'll be plenty of room inside for your bags and cases, and it'll be easy on your pocket too!

Cheap Hotels in Chicago

Ready to start your cheap and chic vacation? Reserve your room right now! CheapTickets has 285 hotels in Chicago.

Why hand over big bucks when you don't need to? Book a room in one our cheap options, like the HI Chicago or the Travelodge by Wyndham Downtown Chicago.

Flight deals to Chicago

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

Tue, May 25
ATL
Atlanta
ORD
Chicago
$27
Spirit Airlines
Wed, Aug 11
LGA
New York
ORD
Chicago
$48
Spirit Airlines
Fri, May 21
ATL
Atlanta
MDW
Chicago
$49
Delta
Thu, May 20 - Tue, May 25
ATL
Atlanta
ORD
Chicago
$53
Spirit Airlines
Thu, May 13 - Mon, May 17
DFW
Dallas
ORD
Chicago
$75
Spirit Airlines
Wed, May 12 - Wed, May 12
ATL
Atlanta
MDW
Chicago
$92
Delta

Top rated hotels for your Chicago vacation

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