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

Wyndham Grand Chicago Riverfront

3 stars
4.2 / 5 257 reviews
This Wyndham Grand Chicago Riverfront effortlessly blends attentive service with chic accommodations for an oasis of comfort and style in the heart of vibrant downtown Chicago. Just steps from The Loop, the cultural district and several renowned business addresses, and convenient to both major airports, this hotel has breathtaking views of the Chicago River and is close to dining, shopping and landmark attractions. Stay connected to colleagues and loved ones with complimentary wireless Internet throughout the hotel. A 24-hour business center lets you take care of work any time, and a 24-hour fitness center lets you stay active. Two onsite restaurants serve all meals as well as room service. Events at this hotel are really special, with a dedicated staff and over 16,000 square feet of sophisticated, customized space including a penthouse ballroom with sweeping views. Oversized guest rooms feature MP3 dock, pillow-top mattress and work area. Pets are welcome. Valet parking is available for 61 USD per night with in/out privileges.
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Nightly rates from $129

The Godfrey Hotel Chicago

4 stars
4.4 / 5 117 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 $129

The Talbott Hotel

4 stars
4.6 / 5 1277 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. Policies and feesGuests must be at least 21 years of age to check in.
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Nightly rates from $131

Virgin Hotels Chicago

4 stars
Not yet reviewed
Deluxe hotel in downtown Chicago with five food and beverage venuesDiscerning travelers looking to explore bustling Chicago find strategic base at the upscale accommodations of Virgin Hotels Chicago. This centrally located hotel places holidaymakers within convenient distance to the business district and go-to points of interests including Millennium Park, Chicago Theater and the lively Navy Pier. For on-site dining options, the property features five restaurant and lounge experiences, including Miss Ricky's, a reinvented American diner, 203, a Euro-style coffee and wine bar and The Commons Club, a lounge and restaurant. Visitors can also unwind with cocktails at in-house The Rooftop Bar, offering scenic city vista. Virgin Hotels Chicago offers three flexible event venues that can host corporate and social gatherings of up to 108 people. After attending to business matters, guests can take a break by working out at the rooftop gym on site. The property also provides complimentary Wi-Fi access for added convenience. 3 Reasons To StayTwo-chamber spacesFree Wi-Fi accessMeeting venues for up to 108 people Virgin Hotels Chicago RoomsVirgin Hotels Chicago boasts modern two-chamber rooms and suites featuring separate bedroom and dressing area with closet and bathroom. All units are outfitted with sliding privacy doors, entertainment system and mini bar. Room service is also provided. Things To Do Chicago Theater (0.09 mi/0.14 km)Oriental Theater (0.2 mi/ 0.3 km)Goodman Theater (0.2 mi/ 0.3 km)Millennium Park (0.3 mi/ 0.5 km)Buckingham Fountain (0.8 mi/1.3 km)Museum of Contemporary Art, Chicago (0.8 mi/1.3 km)Navy Pier (1.0 mi/1.6 km)Shedd Aquarium (1.4 mi/2.3 km)The Field Museum (1.4 mi/2.3 km)Lincoln Park Zoo (2.4 mi/3.8 km)Wrigley Field (4.6 mi/7.4 km)
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Nightly rates from $165

The Silversmith Hotel Chicago

3 stars
4.2 / 5 238 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
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Nightly rates from $105
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Sat, Apr 11 - Tue, Apr 14 $97
Los Angeles Chicago Thu, Apr 16 - Mon, Apr 27 $158
Washington DC Chicago Wed, Apr 1 - Wed, Apr 8 $145
San Francisco Chicago Tue, Mar 31 - Mon, Apr 6 $268
Newark Chicago Tue, Mar 17 - Wed, Mar 18 $188
Atlanta Chicago Tue, Mar 31 - Tue, Apr 7 $107
Seattle Chicago Tue, Mar 31 - Sat, Apr 4 $262
Boston Chicago Sat, Apr 4 - Tue, Apr 7 $161
Dallas Chicago Tue, Apr 7 - Tue, Apr 21 $81
Denver Chicago Wed, Mar 18 - Tue, Mar 31 $97
Phoenix Chicago Wed, Apr 15 - Tue, Apr 21 $98
Orlando Chicago Thu, Mar 19 - Tue, Mar 24 $185
San Juan Chicago Wed, Apr 22 - Wed, May 6 $338
Mexico City Chicago Thu, Apr 9 - Thu, Apr 16 $364
Philadelphia Chicago Mon, Mar 16 - Mon, Mar 23 $138
San Diego Chicago Fri, Apr 24 - Wed, May 6 $227
Fort Lauderdale Chicago Wed, Apr 22 - Fri, Apr 24 $199
Las Vegas Chicago Sat, Mar 7 - Tue, Mar 10 $222
Guadalajara Chicago Fri, Mar 6 - Fri, Mar 13 $427
Tampa Chicago Thu, Mar 19 - Tue, Mar 24 $162
Houston Chicago Mon, Apr 20 - Tue, Apr 21 $120
Baltimore Chicago Sat, Mar 7 - Sat, Mar 14 $187
Honolulu Chicago Sun, Apr 26 - Sun, May 10 $711
Orange County Chicago Wed, Apr 8 - Tue, Apr 14 $295
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  • 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.

  • 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
  • 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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