An Introductory Guide to Chicago in January

Beat the cold with these hot tips for a great getaway in the Second City

Addison Russell, Chicago Cubs, Second Base
Dilip Vishwanat, Getty Images

With the holidays over, Chicagoans settle back into their regular routines in January, which means everything becomes a little less hectic. It also means that if you're considering a weekend getaway to the Windy City, you're likely to stumble across some attractive hotel and airfare deals during the first month of the year.

Highly anticipated theater openings, plus the annual Chicago Restaurant Week, and Cubs and White Sox conventions entice locals out into the cold for some distinctive Chi-Town fun, too.

January Weather in Chicago

Chicago weather in January gets downright cold, ranging from an average high of 30 F to an average low of 15 F. Pack layers of clothing, and bring a winter coat, hat, gloves, and a scarf. An average of 10.99 inches of snow falls in January, so bring comfortable boots if you plan to walk a lot.

You could encounter flight delays/travel problems if a major snowstorm blows through; fortunately there are plenty of options for dining and drinking if you get stranded at Midway or O'Hare airports.

January Perks in Chicago

Mid-winter guests often enjoy lower rates at revered hotel properties such as Conrad Chicago, Soho House, and W Chicago-LakeshoreChicago Restaurant Week runs January 26 through February 8, 2018, and offers prix-fixe deals at 370 dining destinations. You can also join the expected 100,000 people who go ice skating at Millennium Park below Chicago's Cloud-Gate sculpture throughout the winter.

January Accommodations in Chicago

With the holiday rush over, travelers can find availability and good pricing at many of Chicago's iconic downtown hotels.

  • Originally opened in 1890 as an exclusive men's club, Chicago Athletic Association Hotel now operates as a luxury lifestyle hotel with 241 guest rooms catering to well-heeled men and women. Its dining and drinking establishments and its premier location on Michigan Avenue across from Millenium Park attract locals as well. Milk Room, an eight-seat microbar, serves pastries and coffee during the day and high-concept cocktails by night. Game Room houses two bocce courts, pool tables, and table games; and Cherry Circle Room is a cocktail-focused, all-day restaurant.
  • Located in a vintage building constructed in 1927, Freehand Chicago is a Miami import. The property, located in the bustling River North neighborhood around the corner from Shops at North Bridge, includes both private and shared guest rooms. In addition to lodging, the hotel operates Integral Cafe and the eclectic, Polynesian-themed cocktail lounge, The Broken Shaker.
  • Some of the most acclaimed eateries and cocktail lounges are located in the hipster neighborhood of Logan Square, so if you don't want to spend most of your vacation dollars in taxi fare, you can book one of the six rooms at Longman & Eagle Inn. Located directly below the small but contemporary rooms is the Michelin-starred Longman & Eagle restaurant. For more dining and drinking choices, you could head to the nearby Billy Sunday, Fat Rice, Lost Lake, Lula Cafe, Scofflaw, Webster's Wine Bar, or Yusho.
  • The Blackstone has played host to a number of U.S. presidents, dignitaries, celebrities, and other notables, including Katherine Hepburn and Al "Scarface" Capone. The Spanish-inspired Mercat a la Planxa restaurant is on the lobby level.
  • Virgin Hotels Chicago. The world's first-ever Virgin hotel is located downtown, and positions itself to be a "lifestyle" experience with a handful of restaurants and drinking destinations. The property features dog-friendly chambers equipped with dog beds.

January Highlights/Events in Chicago

The weather gets brutally cold in Chicago in January, but that does not stop the locals from fully enjoying their lively city with a robust calendar of activities and events.

  • Chicago's biggest and best indoor winter playground, Winter WonderFest at Navy Pier, runs through January 8, 2018, with rides, slides, and an ice skating rink.
  • The 33rd Annual Chicago Cubs Convention January 12 to 14, 2018, brings player meet-and-greets, autograph signings, and interactive exhibits to the public at the Sheraton Grand Chicago.
  • The Black Creativity Juried Art Exhibition at Museum of Science and Industry runs from late January through February, 2018, and presents more than 100 works of art by emerging and professional African-American artists.
  • The 26th annual fan convention, SoxFest Chicago takes place January 26 to 28, 2018, at the Chicago Hilton with former Sox stars and current players on hand to sign autographs and participate in Q&A sessions.