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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Hotel only
Nightly rates from $75

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

Hotel Rush

3 stars
4.1 / 5 176 reviews
Access to attractions, plus free Wi-Fi and indoor poolGuests at the Hotel Rush enjoy a plum location just off the Magnificent Mile. Whether the agenda is hitting downtown shops, restaurants, bars or landmarks, leisure travelers will find no shortage of distractions nearby while executives enjoy convenient access to the Loop and the Financial District. With standard amenities like complimentary Wi-Fi throughout the property, an indoor pool and fitness and business centers, the property stands as a well-rounded option for budget-minded vacationers. Highlights Close to the Magnificent MileComplimentary Wi-Fi throughout the propertyIndoor pool24-hour business centerSushi restaurant and artisan breakfast and lunch eatery onsite RoomsSmoke-free rooms at the Hotel Rush are airy and open with windows that look out to the city. Plump duvets boast a subtle beige plaid print that matches extra seating, curtains and artwork around the room. In every space, expect complimentary Wi-Fi or hardwired access, plus extras such as refrigerator, microwave, desk and free bottled water. For extra comfort, visitors can request a room with a balcony, whirlpool or wet bar. FeaturesVirtual office. Night on the town. Quick lunch. Energizing workout. Hotel Rush answers all these needs. A 24-hour business center is open for checking email, printing an agenda or sending an important document via fax. Craving a healthy snack before hitting the Magnificent Mile? Try e.leaven Food Company for artisan pastries, omelets, salads and sandwiches. For people-watching, head to Sushi Taiyo, where inventive rolls complement rice and noodle dishes. Guests whose routine requires a daily dose of cardio can work out in the 24-hour fitness center equipped with Life Fitness machines or swim laps in the indoor pool with skylights and windowed views of the city. Transportation O'Hare International Airport (17 miles)Midway Airport (13 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (10 minutes) Attractions Magnificent MileRush StreetGold CoastMillennium ParkGrant ParkJohn Hancock CenterNavy Pier Business 4,000 square feet of meeting spaceCatering by Lawry's Prime Rib, e.leaven Food Company and Sushi Taiyo24-hour business centerComplimentary high-speed wired and wireless Internet access Terrace available for seasonal events Policies and feesThe lobby will undergo refurbishments from 19 January until 20 March 2015.
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Nightly rates from $95

Red Roof Inn Chi Downtown Magnificent Mile

2 stars
2.9 / 5 173 reviews
Red Roof Inn Chicago Downtown Magnificent Mile, Illinois is a pet friendly, family friendly hotel. This hotel is near Michigan Ave. in Chicago, IL and close to the Chicago Loop/US-41. Check in age is 21 years or older. Fee for Parking and Valet.
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Hotel only
Nightly rates from $66

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 $99
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Wed, Apr 1 - Sat, Apr 11 $107
Los Angeles Chicago Tue, Apr 14 - Wed, Apr 29 $158
Washington DC Chicago Wed, Apr 22 - Sat, Apr 25 $112
San Francisco Chicago Fri, May 1 - Tue, May 5 $198
Newark Chicago Sun, Apr 26 - Wed, Apr 29 $177
Atlanta Chicago Tue, Mar 31 - Wed, Apr 1 $98
Seattle Chicago Tue, Apr 28 - Tue, May 5 $241
Boston Chicago Tue, May 5 - Wed, May 6 $127
Dallas Chicago Sat, Apr 18 - Wed, Apr 22 $81
Denver Chicago Sat, Apr 25 - Tue, Apr 28 $97
Phoenix Chicago Wed, Apr 22 - Tue, Apr 28 $118
Orlando Chicago Tue, Mar 17 - Tue, Mar 24 $172
San Juan Chicago Tue, Apr 28 - Wed, May 6 $338
Mexico City Chicago Sat, Apr 25 - Thu, Apr 30 $255
Philadelphia Chicago Mon, Mar 16 - Tue, Mar 17 $98
San Diego Chicago Tue, Apr 21 - Tue, Apr 28 $197
Fort Lauderdale Chicago Wed, Apr 29 - Mon, May 4 $157
Las Vegas Chicago Wed, Apr 22 - Tue, Apr 28 $137
Guadalajara Chicago Thu, Mar 12 - Tue, Mar 17 $372
Tampa Chicago Tue, Apr 21 - Thu, Apr 23 $132
Houston Chicago Wed, Apr 8 - Wed, Apr 15 $79
Baltimore Chicago Wed, Apr 22 - Wed, Apr 29 $157
Honolulu Chicago Tue, Apr 7 - Mon, Apr 13 $651
Orange County Chicago Tue, Apr 14 - Tue, Apr 21 $231
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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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