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Cool Ways to Save in the Windy City

Jan 03, 2020 Chicago

Group of friends drinking wine and talking to each other.

For a budget-friendly getaway, visit Chicago this winter when restaurants, theaters, hotels and museums drop their prices. Here are some special Chicago events and other tips that will save you a bundle.

Chicago Restaurant Week

It’s called a “week,” but the annual Chicago Restaurant Week is actually more than two weeks of excellent deals (January 24–February 9). 

Nearly 400 restaurants with a variety of price points and cuisine types offer price-fixe menus (excluding beverages, tax and gratuity). Look for high-end, award winner Boka, buzzed-about newcomer Le Sud, famous steakhouse Gene and Georgetti Steakhouse, and places with gorgeous skyline views like Everest

Eating out during Restaurant Week is a great way to sample a new ethnic cuisine, or splurge on a fancy restaurant, without paying full price. Participating restaurants post menus online, which allows you to determine where you’ll get the best deal.

Reservations at popular restaurants go quick, plan to reserve a table when they start accepting reservations. Even if you decide to dine out at last minute, without reservations, you’ll still find lots of tasty—and budget-friendly—options.

A group of people roasting marshmallows at Geja's Cafe.

Chicago Theatre Week

Ticket prices go down before the curtain goes up during Chicago Theatre Week, a 10-day event (February 13–23).

For less than the price of a deep-dish pizza, you can see one of Chicago’s renowned comedy, dance and theater performances. Ticket prices are slashed for roughly 100 performances in the city and suburbs, both in the large, grandiose theaters and the casual, intimate ones. 

Chicago Theatre Week tickets sell out for popular shows like Second City, Broadway Musicals or Blue Man Group. Plan to purchase as soon as they go on sale in January. For a preview of shows with deals, subscribe to Chicago Theatre Week’s email list or follow @ChicagoPlays on Twitter.


Year-Round Deal

For half-price tickets, HotTix to the rescue. While the inventory changes daily—and there are many big-name, high-quality shows on the list—it’s rare to find tickets for the hottest shows. To find out what’s available, even the day before or day-of the show, check the HotTix website or walk up to one of their two downtown locations (72 E. Randolph, across from Millennium Park, or 108 N. State Street, in the theatre district).  

People going to attend the opera at Lyric Opera House.

Free Museum Days

Get a history and cultural lesson for free at some of the city’s best-known museums. Some require visitors be a resident of Illinois and show proof of residency to enjoy free admission. Veterans and military families enjoy even more perks. Click here for the entire 2024 list.



Thursday, 5–8 p.m.

First Sunday of the Month

Random days, check the schedule

Hotel deals

Chicago added more than 2,000 new hotel rooms in 2019, which means there’s a bump in supply and competitive pricing. The best time of year to find cut rates is between now and early March. Good last-minute deals can be found on the Hotel Tonight app and website. You can stay for as low as $50 a night if you’re willing to share communal spaces or a room in stylish hostels like Freehand Chicago and Found Hotel.

Another cost-saving option is to look at hotels beyond the downtown area. Hotels near the “L” train in neighborhoods like Wicker Park, Wrigleyville or Bucktown, or neighboring suburbs like Rosemont, are often less expensive.

Other freebies

For other cost saving options, check out Chicago’s Greeter Program for a variety of free tours.


Content provided by Jamie Bartosch

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