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

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 261 reviews
The Inn of Chicago, a landmark building recently transformed into a sleek and contemporary design, is located in the heart of the Magnificent Mile in downtown Chicago, 1/2 block from Michigan Avenue, easy walking distance to Navy Pier, Millenium Park, State St. shopping and right in the heart of downtown corporate offices. This is the perfect location for business and leisure travelers seeking Michigan Avenue accommodations and convenient access to world reknown shopping, entertainment and the best restaurants that Chicago has to offer. Michigan Avenue is calling you to visit us. Internet charge in rooms: 9.95 /day. Off site Indoor Parking: 1/2 block from hotel. Self Parking: 36.00 per day Valet Parking: 41.00 per day.
Flight + Hotel
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Nightly rates from $95

River Hotel

3 stars
3.9 / 5 373 reviews
Perfect location at the top of the Magnificent mileAs locations go, this Wacker Drive hotel couldn't do better, occupying prime riverfront space in the historical Mather Tower off the Magnificent Mile. The landmark River Hotel has kept up with the times, especially when it comes to environmental impact. Its LEED-registered building and Green Power Partner utilizes low-flow showerheads and participates in recycling programs. For what it may lack in luxury and size, the hotel scores on points like casual ambiance, simplicity and value. Highlights LEED-registered hotel with green design and practicesKitchenettes available, plus free chilled, purified bottled waterDelivery from select neighborhood restaurants Bella Bacino's Italian Bistro & PizzeriaFree high-speed wireless Internet access throughout the hotel RoomsWell-kept, comfortable rooms at the River Hotel offer the no-frills traveler twin, full, premium queen and king beds, plus work station. Some rooms are equipped with kitchenettes, and corporate apartments are available for professionals seeking accommodations for longer than a month.   FeaturesNot every professional has an expense account and travel-related costs can really add up -- lodging, food and transport to name a few. For the conservative business traveler, the River Hotel offers a great value with special perks like free wireless Internet access and complimentary chilled, purified bottled water. The River Hotel has a convenient location in Chicago, steps from the Magnificent Mile, Tribune Tower, Millennium Park and the Loop for business travelers.Other features include a 24-hour concierge, and fitness room. Bella Bacinos, a casual Italian-American trattoria, is open for breakfast, lunch and dinner. Valet and self-parking are available for a fee. TransportationO’Hare International Airport (15.6 mi/25.2 km)Chicago Midway Airport (9.5 mi/15.3 km)Blue Line (Clark/Lake) (0.3 mi/0.5 km)Orange Line (State/Lake) (0.2 mi/0.3 km)McCormick Place Convention Center (2.5 mi/4.1 km) AttractionsTribune Tower (0.2 mi/0.3 km)Wrigley Building (0.2 mi/0.3 km)Millennium Park (0.4 mi/0.6 km)The Magnificent Mile (0.4 mi/0.7 km)The Loop (0.5 mi/0.8 km)Board of Trade (0.7 mi/1.2 km)Chicago Mercantile Exchange (0.8 mi/1.2 km) BusinessThree meeting rooms24-hour concierge Same-day dry cleaning and laundry serviceComplimentary high-speed wireless Internet access throughout the hotel
Value Save 12% on your stay
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Nightly rates from $89

La Quinta Inn & Suites Chicago Downtown

3 stars
4.0 / 5 126 reviews
Nestled in the heart of Chicago's financial district, just two blocks from Sears Tower, the all-new La Quinta Inn & Suites Chicago Downtown offers convenient access to popular Chicago attractions in addition to upscale services that will keep you refreshed and productive. Shopping, dining, and entertainment venues are within easy reach thanks to the hotel's close proximity to public transportation and downtown attractions (such as the theater district). Walk to the Sears Tower and choose from a variety of area restaurants including Argo Tea Company, Pot Belly, and Chipotle (all adjacent). Shop at nearby State Street Mall or The Magnificent Mile before heading to a game at United Center (Chicago Bulls, Blackhawks), US Cellular Field (Chicago White Sox), Wrigley Field (Chicago Cubs), or Soldier Field (Chicago Bears). Enjoy free wireless high-speed Internet access, a 24-hour business center, well-equipped fitness center, refreshing indoor swimming pool, and much more at the La Quinta Inn & Suites Chicago Downtown. Take advantage of our Free Bright Side Breakfast, each morning of your stay. La Quinta Returns' members are welcomed with express check-in and a free newspaper delivered to their room. In addition to free wireless high-speed Internet access, each spacious guest room includes a 32-inch flat-screen TV w/popular cable channels (including radio channels), coffee maker, hair dryer, iron w/ironing board, free local calls, and more. King bedded guest rooms and suites also include a microwave and mini-refrigerator. The La Quinta Inn & Suites Chicago Downtown features a contemporary design that is both functional and environmentally friendly. This location participates in the city's Green Roof Program. Green roofs help keep cities healthy and help conserve energy because they work to lower surrounding urban heat temperatures.
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Nightly rates from $139

The Talbott Hotel

4 stars
4.6 / 5 1278 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.
Value Last Minute Deal!
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Nightly rates from $123

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 $94
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Tue, May 5 - Sat, May 9 $107
Los Angeles Chicago Tue, Apr 14 - Tue, Apr 21 $248
Washington DC Chicago Wed, Mar 18 - Wed, Mar 25 $167
San Francisco Chicago Thu, Apr 30 - Tue, May 5 $244
Newark Chicago Sun, Apr 26 - Mon, Apr 27 $183
Atlanta Chicago Wed, Apr 8 - Tue, Apr 14 $107
Seattle Chicago Wed, Apr 1 - Wed, Apr 8 $257
Boston Chicago Tue, Apr 28 - Tue, May 5 $127
Dallas Chicago Wed, Apr 1 - Tue, Apr 7 $81
Denver Chicago Sat, Apr 25 - Tue, Apr 28 $97
Phoenix Chicago Thu, Mar 19 - Tue, Mar 31 $190
Orlando Chicago Wed, Apr 22 - Mon, Apr 27 $167
San Juan Chicago Wed, Apr 15 - Mon, Apr 20 $363
Mexico City Chicago Mon, Apr 27 - Mon, May 4 $255
Philadelphia Chicago Sat, Apr 18 - Tue, Apr 21 $137
San Diego Chicago Tue, May 5 - Wed, May 13 $197
Fort Lauderdale Chicago Wed, Apr 22 - Fri, Apr 24 $179
Las Vegas Chicago Wed, Apr 22 - Tue, Apr 28 $137
Guadalajara Chicago Sat, Apr 18 - Sun, May 17 $311
Tampa Chicago Wed, Apr 29 - Mon, May 4 $167
Houston Chicago Wed, Apr 29 - Wed, May 6 $79
Baltimore Chicago Sat, Apr 18 - Wed, Apr 22 $167
Honolulu Chicago Tue, Apr 7 - Sun, Apr 12 $651
Orange County Chicago Wed, Apr 8 - Mon, Apr 13 $309
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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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