Cheap Chicago Vacations

Chicago

Your Chicago vacation

From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

Cheap Vacation Packages

Cheap Chicago Vacation Packages

Hilton Garden Inn Chicago Downtown North

3 stars
4.0 / 5 106 reviews
Business and leisure hotel with free Wi-Fi near the Magnificent Mile Business and leisure travelers target this Streeterville hotel for its proximity to the Magnificent Mile, only a few blocks away. The three-star Hilton Garden Inn Chicago covers all the basics: well-kept rooms, complimentary Wi-Fi throughout and a place to dine. Weber Grill of backyard barbecue fame invites diners to sample its signature charcoal fired steaks, burgers and chicken. Other must-sees aren't far away, like the family-friendly Navy Pier, the Loop, the Financial District and McCormick Place. Highlights Free Wi-Fi in the lobby and roomsSkylit indoor pool and JacuzziClose to the Magnificent Mile, Navy Pier and other classic Chicago gems7,000 square feet of meeting space RoomsRooms at Hilton Garden Inn are 300 square feet, configured with a large king or two queen beds, all of which feature the Garden Sleep System. For added comfort, each room includes a comfortable chair and ottoman, generous work desk and Herman Miller chair, flat-screen TV, individual climate control, microwave, refrigerator and complimentary high-speed Internet access. Guests who prefer rooms with a skyline view can make the request at check-in. FeaturesIf a hotel's priority is to create a second, albeit temporary home for guests, then visitors at the Hilton Garden Inn Chicago Downtown North will be pleased. In addition to a business center and classic American restaurant (Weber Grill), the hotel provides an ATM, a 24-hour pantry for sundries, laundry and valet service and car rental services. Oh, and don't forget to pick up free cookies between 5 p.m. and 7 p.m. Transportation O'Hare International Airport (16 mi/25.8 km)Midway Airport (12 mi/19.3 km)Closest train stops: Blue Line (Jackson to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (2.8 mi/4.5 km) Attractions  Magnificent Mile River NorthNavy PierMuseum of Contemporary ArtMillennium Park Grant ParkShedd AquariumAdler Planetarium Business 7,000 square feet of function space on the 12th floor with views of the Chicago skylineBusiness center with computers, copier, fax machines and printersConference services staff and audiovisual team Policies & feesThe pool is closed for renovation. Guests can use the pool across the street at the sister hotel Embassy Suites by Hilton. Hilton Garden Inn apologizes for any inconvenience this may cause.
Value Complimentary wired and Wi-Fi Internet Access
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Nightly rates from $89

Embassy Suites Chicago - Downtown

3 stars
4.1 / 5 104 reviews
At Embassy Suites Chicago Downtown, you’re in the heart of downtown Chicago, Illinois, surrounded by shopping and entertainment venues on all sides. Located on State Street between Ohio and Ontario Streets, we’re three blocks west of Michigan Avenue's Magnificent Mile, and convenient to the Loop, the financial district and popular attractions. A block away is the free seasonal Navy Pier trolley and subway, linking to local attractions and both Midway and O'Hare airports. A great choice in Chicago hotels, this downtown all-suites property is convenient to Boeing, the Chicago Board of Trade, City Hall, IBM, Prudential Plaza and Sears Tower.Start the day with complimentary cooked-to-order breakfast. Relax in a two-room suite, complete with a separate lounge, refrigerator, microwave and high-speed internet access. Unwind at our Complimentary Evening Reception, which includes a range of beverages and snacks*. Sample Italian specialties at Osteria Via Stato and Pizzeria Via Stato. Maintain any exercise routine in the complimentary fitness center, and melt away stress in the indoor pool and whirlpool.Plan your meeting, wedding or special event in the heart of the city for 300 guests at our Chicago hotel, downtown on State Street. In addition to our business center, utilize our video conferencing, webcasting, and teleconferencing services.*Service of alcohol subject to state and local laws. Must be of legal drinking
Value Free cooked-to-order breakfast, Evening Reception
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Nightly rates from $89

The Silversmith Hotel Chicago

3 stars
4.2 / 5 233 reviews
Landmark in the Loop near attractions and shoppingIt's only fitting that this historic hotel is just a few blocks from Jewelers Row given its name and former purpose. In the 1890s, its tenants worked in the jewelry and silver trade. Today, landmark elements -- a cast iron staircase, terra cotta touches -- give the Silversmith Hotel Chicago a unique architectural identity. Ideally situated near the Magnificent Mile and Millennium Park, the Silversmith Hotel Chicago appeals to budget-minded travelers seeking quick access to Chicago's most popular attractions. Highlights One block to the Magnificent Mile, Millennium Park and State Street shopping24-hour fitness centerFree high-speed Internet access throughout the hotelDining at Ada's Deli & Restaurant and cocktails at the 14 Karat LoungeHistoric, independent hotel with Arts and Crafts style RoomsRooms and suites at the Silversmith Hotel Chicago serve their purpose, providing comfortable beds and a place to freshen up in between sightseeing excursions. The hotel’s 12-foot ceilings add dimension, while 10-foot picture windows view the city and the El. Wood headboards, desks and Prairie-style lamps complete the casual look. Complimentary wireless Internet access is available throughout the property. FeaturesIntimate and under the radar, the Silversmith Hotel Chicago does not fit the trendy boutique mold, but guests will appreciate its location. No less than a dozen attractions are within walking distance, including the theater district, Jewelers Row, State Street, Grant Park and Millennium Park. Transportation O'Hare International Airport (15.8 mi/25.4 km)Chicago Midway Airport (9.2 mi/17.8 km)Blue Line (Monroe/Dearborn to O'Hare) (0.2 mi/0.3 km)Orange Line (Madison/Wabash to Midway) (0.1 mi/0.1 km)McCormick Place Convention Center (2.1 mi/3.5 km) Attractions Jewelers Row (0.1 mi/0.1 km)The Art Institute of Chicago (0.1 mi/0.1 km)Millennium Park (0.3 mi/0.4 km)Grant Park (0.4 mi/0.6 km)State Street (0.6 mi/0.9 km)Field Museum (1.2 mi/1.9 km)Shedd Aquarium (1.2 mi/1.9 km)Adler Planetarium (1.5 mi/2.3 km) Business Executive boardroom hosts up to 12 guestsChicago Landmark Room hosts up to 120 guestsPresentation equipment available, including 34-mm slide projector, flip chart and markers, LCD projector, microphone, VCR, overhead projector, modem lines and white boardsBusiness centerFree high-speed Internet access available throughout the Silversmith Hotel Chicago
Value Save 15% with advance purchase
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Nightly rates from $109

The Talbott Hotel

4 stars
4.6 / 5 1219 reviews
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls. Awarded the Best in Stay Award in 2014 - 2015, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Mercadito Fish Co., and the knowledgeable 'Concierge Blog' on the hotel's site, setting the hotel far apart from other Chicago accommodations. Key facts149 guestroomsPets allowed (up to 50 pounds, and fees may apply)Conference and event spaces: 3 rooms, up to 200 guestsFitness centerLaundry serviceFree Wi-Fi Restaurant/bar: Mercadito Fish Co. NeighborhoodWith a prime location just a few blocks from Washington Square Park, Oak Street and the Magnificent Mile, The Talbott Hotel comes with easy access to shops like Bloomingdale's and Macy's, as well as the scenic Lakefront Trail on the shores of Lake Michigan. The Art Institute of Chicago is less than two miles from The Talbott's front entrance, boasting a staggering collection of over 250,000 works of art, including work by Vincent van Gogh, Claude Monet and Mary Cassatt. Hints and tipsFor privileged views of Chicago and a bit of distance from busy Delaware Street, ask for a room on the upper floors.For a more personalized stay, the Talbott Hotel's packages offer everything from the princess treatment for young daughters - including milk and cupcakes at turndown - to a $50 gift certificate  for the 900 North Michigan Shops.
Value Last Minute Deal!
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Nightly rates from $116

The Godfrey Hotel Chicago

4 stars
4.4 / 5 76 reviews
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience in mind.
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Nightly rates from $99
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Tue, Jan 20 - Tue, Jan 27 $137
Los Angeles Chicago Mon, Jan 26 - Thu, Jan 29 $237
Washington DC Chicago Fri, Jan 9 - Sat, Jan 24 $92
San Francisco Chicago Sat, Jan 17 - Tue, Jan 20 $246
Newark Chicago Sat, Jan 24 - Sat, Jan 31 $245
Atlanta Chicago Fri, Feb 6 - Tue, Feb 10 $108
Seattle Chicago Wed, Feb 4 - Tue, Feb 10 $262
Boston Chicago Wed, Jan 7 - Mon, Jan 12 $133
Dallas Chicago Wed, Jan 7 - Wed, Jan 14 $81
Denver Chicago Thu, Jan 15 - Tue, Jan 20 $81
Phoenix Chicago Sat, Jan 31 - Sat, Feb 7 $145
Orlando Chicago Sat, Jan 17 - Wed, Jan 21 $119
San Juan Chicago Thu, Jan 29 - Tue, Feb 3 $332
Mexico City Chicago Wed, Dec 24 - Wed, Jan 7 $349
Philadelphia Chicago Mon, Jan 19 - Mon, Jan 26 $241
San Diego Chicago Tue, Jan 27 - Tue, Feb 10 $285
Fort Lauderdale Chicago Fri, Dec 26 - Mon, Jan 5 $197
Las Vegas Chicago Sun, Jan 18 - Sat, Jan 24 $182
Guadalajara Chicago Fri, Jan 16 - Mon, Feb 2 $343
Tampa Chicago Wed, Jan 21 - Sun, Jan 25 $97
Houston Chicago Tue, Jan 27 - Sat, Jan 31 $135
Baltimore Chicago Thu, Jan 22 - Thu, Jan 29 $177
Honolulu Chicago Wed, Jan 7 - Wed, Jan 14 $724
Orange County Chicago Tue, Jan 13 - Tue, Jan 20 $261
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Best time to take a vacation to Chicago

  • If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

Insider tips for Chicago travel

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

Chicago highlights

  • Chicago highlights
  • Navy Pier

    For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

  • Magnificent Mile

    The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

  • Lincoln Park Zoo

    For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

  • Cultural Chicago

    If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

  • Millennium Park

    Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

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