Chicago Illinois Hotel Deals: How to Score the Best Prices

A city of grit, steel, and some wildly delicious pizza, it’s no wonder that Windy City hosts almost 50 million visitors each year. However, a stay in Chicago doesn’t always come cheap.

Lake Michigan cruises, architecture tours, plus visits to the Skydeck can quickly add up.

Keep your vacation budget afloat when you utilize the best Chicago Illinois hotel deals.

Discovering the best hotel deals in Chicago is one of the foremost ways to save during your Chi-town getaway.

Thankfully, our team of super savers has done the work to bring you the top cheap Chicago hotel rates and the premier Chicago, IL, hotel deals.

Whether you want lodgings just a stone’s throw from the Magnificent Mile, or would rather sacrifice location for hotels with free parking, we have the details on every type of cheap Chicago Hotel.

Book last minute and score lower prices for sumptuous 4-star hotels that feature indoor pools, spas, and spacious suites. Or, stay thrifty with a budget inn in Schaumburg.

Ready to snag your very own hotel discount in Chicago, IL? Read on!

Hotel Deals in Chicago

Plane tickets are purchased and you’ve been lucky enough to lock down White Sox tickets. Now what? The first step to securing your dream hotel in Chicago for a thrifty price is to access your Chicago itinerary needs.

Depending on the nature of your Windy City visit you may have more or less wiggle room when it comes to the time of year, week, or day you travel. Furthermore, if you plan to have your own transportation you may be more inclined to stay outside the city limits and save a buck or two.

Before we dive into the nitty gritty of super saving in the Second City we suggest getting a rough idea of your Chi-town bucket list. Whether you have your heart set on munching your way through the Bean or wish to while away your day admiring masterpieces at the Art Institute, this will inform where you stay.

Psst…On the hunt for even more things to do in Chicago? Check out our full array of Windy City attractions and activities.

wide view of navy pier with the skyline in the background in Chicago, Illinois, USAHow to Find Chicago Hotel Deals

All set to enjoy your week of Night Crime Tours and percussion-based Blue Man Group performances? Make sure you have even more leftover dough when you utilize our best tips and tricks for cheap hotel deals in Chicago:

Time of Year

We hope you like long johns! While snow and sleet aren’t everyone’s cup of tea, the benefits of a winter Chicago vacation are twofold. Visitors hightailing it to the Windy City from November through March will need to bundle up to brave the frigid temperatures.

Nonetheless, they will be blessed with lower lodging rates and fewer crowds. Conversely, the high season in the Second City is summer. Along with these balmy temperatures, tourists will be treated to an abundance of outdoor activities, festivals, and events.

Related Post: Skydeck vs 360 Chicago: Which Chicago Observation Deck Should You Visit?

Unfortunately, this peak travel season will also warrant inflated prices. For an ideal balance of weather, crowds, and cost, visitors can aim to set foot in Chi-town anywhere from April through May or between September and October.

ground view of people walking past cloud gate bean in Millennium Park in Chicago, Illinois, USA
phot credit: Cloud Gate via Facebook


Location, location, location! This sparkling jewel of the Midwest is home to a number of charming neighborhoods from Wicker Park to River North. Obviously, the most desirable areas of the city will come with a higher price tag.

Savvy travelers know that it pays to do a bit of research on ‘hotel rooms downtown Chicago’ before committing to a deal. As a general rule, lodgings located in close proximity to the city’s main attractions, such as the Navy Pier, Millenium Park, and the Willis Tower, will always cost a pretty penny.

Many times visitors can cut down on their accommodation expenses by looking for hotel deals near Chicago. Adjacent Chi-town cities such as Schaumburg are situated right by the O’Hare International Airport and deliver a bevy of wallet-friendly options. However, do keep in mind that depending on traffic, you may face up to an hour (or more) of commuting time to arrive in the city.

Another way to narrow down your selection of hotels downtown Chicago is to choose lodgings near public transportation stops. Chi-town public transit is some of the best in the country, and as long as you have easy access to a metro hub, you should be able to scurry all over the city stress-free.

Last Minute Hotel Deals Chicago

Calling all of our spontaneous travel planners! If you love a spur-of-the-moment getaway, you may just be in luck. While many times it pays to plan your airfare and accommodations two to four months in advance, sometimes last-minute travel lodgings can be achieved for a significantly lower price.

Related Post: Go City Chicago Explorer Pass: Discounts, Tips, and Reviews

We recommend checking out the best deals for Chicago Hotels a few nights before your trip to see what last-minute discounts are in store. Thanks to hotel specials in Chicago, you could be privy to savings of up to $245.21 per night.

Please note that last-minute hotel bookings do come with some degree of stress and uncertainty, so only aim for this option if you have a moderate amount of flexibility within your plans.

chicago river with buildings and skylineDowntown Chicago Hotel Packages

Looking to really dig your teeth into the soul of the Second City? Make the most out of your Midwestern adventure, when you jam-pack your Chicago trip full of top-notch attractions and sights.

Dive deeper into the history, architecture, and diverse culinary scene of Chicago, and save on your accommodations when you bundle the two. Combining your hotel reservation with your choice of attractions can earn you savings of up to 25%.

Watch in awe as azure-colored men make mesmerizing music out of PVC pipes, or hop along a Big Bus tour to uncover the intricacies of Magnificent Mile, Field Museum, and the Adler Planetarium.

From medieval feasting and jousting to days spent crafting the perfect brick creations at LEGOLAND Discovery Center, there are endless ways to see every favorite Chi-town sight and save:

Exterior view of the Lincoln Park Conservatory in Chicago, Illinois, USA
photo credit: Lincoln Park Conservatory via Facebook

Discount Hotels Chicago

Are your fingers going numb from scrolling through countless searches of ‘Chicago hotel cheap’ or ‘downtown Chicago hotel deals?’ Give those digits a rest, as we’ve combed through a massive selection of hotel deals in downtown Chicago and beyond to bring you our best contenders for Windy City discount lodgings.

No matter if you are looking for a modest suite just moments from the airport, or want to settle into a cozy bed and breakfast complete with freshly baked biscuits, we offer accommodations for every type of traveler.

Comfort Inn Chicago Schaumburg – O’Hare Airport

Cozy, comfortable, and featuring a plethora of amenities, this suburbs-based inn in Schaumburg offers the perfect launch pad for families looking to frequent LEGOLAND Discovery Center or Medieval Times Dinner & Tournament.

The Comfort Inn Chicago Schaumburg – O’Hare Airport is a mere 27.4 miles from downtown Chicago and is completely fido-friendly. Hotel guests can check up on email using the free wifi or score a wholesome free breakfast of waffles, eggs, and more.

Take a refreshing dip in the indoor heated pool, and don’t forget to inquire about their airport shuttle service when your time in the Windy City is done.

A picture of a bed and a living room
photo credit: Club Quarters Hotel Wacker at Michigan, Chicago via Facebook

DoubleTree by Hilton Hotel Chicago – Schaumburg

The name you trust with a price tag that makes you smile! Relish the modern, minimalistic furnishings when you come home to your tastefully appointed DoubleTree by Hilton Chicago room in Schaumburg.

Part of the Hilton Chicago family, hotel guests will be able to kick back and relax after a day of sightseeing thanks to their indoor pool, on-site restaurant, and 24-hour fitness center.

Business travelers can take advantage of over 2,700 square feet of flexible meeting space. Meanwhile savvy shoppers will appreciate being less than a mile away from the retail, dining, and entertainment at Woodfield Mall.

Country Inn & Suites by Radisson

Free parking and wifi make the Country Inn & Suites by Radisson an excellent choice for travelers in the know. Cuddle up in your king suite complete with a fireplace, as you peruse the offerings on cable TV.

Kick off your day of Chi-town exploration with a hot breakfast, or be sure to swing by the manager’s evening reception for complimentary snacks and beverages Monday through Thursday.

Related Post: Nightlife in Chicago – 13 Unexpected Things to Do After Dark

Soothe tired muscles with a long soak in the hot tub, or sneak in some heart-pumping cardio in the fitness center. Ideal for groups looking to attend a royal feast, the Country Inn is located just a few miles from Medieval Times Dinner and Tournament.

View of a very clean beige and brown hotel room with flowers on the bed and a large window with the curtains open on.Hilton Garden Inn Schaumburg

A stunningly elegant lobby envelopes  Hilton Garden Inn Schaumburg guests into a world of modern comfort and ease. Save plenty of cash, and enjoy a medley of onsite amenities and perks when you make a date with this Hilton Chicago property.

From free self-parking to an on-site game room, guests of all ages will find plenty to do. Easily attend events at both LEGOLAND Discovery Center Chicago and Medieval Times. Or, take advantage of the furnished rooms complete with mini-fridges and microwaves.

Steal away for a bite at the Garden Grille & Bar, or make the less than 30-mile drive into the Windy City to savor the views from 360 Chicago.

Hotel Felix

Eco-friendly lodgings for a steal? All of our earth warriors will be pleased to check into downtown Chicago’s first hotel with a Silver LEED certification from the U.S. Green Building Council. Located in Chicago’s trendy River North neighborhood.

Hotel Felix puts you within walking distance of the Magnificent Mile, Water Tower Place, and the Chicago Theater. Head back to your polished room outfitted with stylish earth-tone furniture and decor. Or stop by the lobby for an early morning coffee or tea.

Feel free to bring along any furry friends, as Hotel Felix is a pet-friendly establishment.

Chicago skyline aerial drone view from above, lake Michigan and city of Chicago downtown skyscrapers cityscape, Illinois, USAHouse 5863 Bed and Breakfast

Who says B&Bs need to contain creaky rocking chairs and antiquated Victorian decor? Savor all of the homey perks of a real Bed and Breakfast within the city, when you stay at House 5863 Bed and Breakfast.

A contemporary, urban take on a traditional B&B, the House showcases vibrant rooms exploding with art, color, and style. Take a break in the common area and catch up on your reading. Or head to the garden and deck for some sunshine.

Related Post: 3 Days in Chicago: How to Make the Most of 72 Hours

Devour their complimentary breakfast featuring freshly baked biscuits. Or head out to discover nearby attractions such as Rosehill Cemetery, Gethsemane Garden Center, and the Redtwist Theatre.

The Congress Plaza Hotel

Hear that sizzle? Embrace the red-hot savings of the Congress Plaza Hotel when you make your booking now. A true luxury hotel and a Chi-town staple. Guests will be mesmerized by the gilded arches, chandeliers, and impeccably designed rooms of this iconic Windy City establishment.

Located right on Michigan Avenue, this premier hotel has played host to everyone from foreign dignitaries to U.S. presidents. Relish your unparalleled downtown location as you soak in Lake Michigan views from your room. Or stroll on over to such hotspots as the Buckingham Fountain, The Field Museum, the Shedd Aquarium, and the Art Institute.

exterior of Congress Plaza Hotel at night with neon red sign and street lamps on ground and statue of man on horse in foreground in Chicago, Illinois, USA
photo credit: Pam Pole via Facebook

Home to Al Capone, the White Sox, and tons of groundbreaking Frank Lloyd Wright architecture. Chicago is a city that has always captured the imagination of America.

While planetarium visits and Chinatown food tours may do some damage to your Chi-town vacation fund. There are plenty of ways to save when it comes to your Windy City lodgings.

Dial in your savings when you brave frigid 16-degree Fahrenheit temperatures and ring in the new year in the Second City. Or, escape to the Chicago suburbs and spend hours enjoying nearby LEGOLAND and Medieval dinner attractions.

No matter if you are looking for sleek urban lodgings for a low price. Or want to cut down on your airport commute, Tripster offers the very best Chicago hotel deals.

Tell us, When is Your Next Chicago Trip?

Leave a comment below and mention which hotel deals Chicago you’ll use next!

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Written by Isis Maya Nissman

A New York native, Isis-Maya spent most of her professional life working in TV production until a vacation whisked her away to Central...

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