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

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1120 reviews
With its neon-red sign standing out against the Chicago skyline, its vaulted Italianate ceilings, and glimmering 'Gold Room' banquet hall, the Congress Plaza Hotel makes an imposing first impression. Once known as the "Home of Presidents" due to its popularity with both Roosevelt's, Woodrow Wilson and Richard Nixon, it's been operating since 1893. Valet dry-cleaning and barber services of yesteryear sit side-by-side with modern amenities like audiovisual tech for business meetings and a 24-hour fitness center. On-site eating options are globally diverse (Rafael's Steakhouse) and come straight from the griddle in the morning (Gazebo Restaurant). In the evenings, settle into a leather back armchair with a bourbon, or take your shots at the dartboard in the Congress Lounge, where both business users and vacationers gather for some much-needed R&R. Key facts871 guestrooms36 suites23 meeting/event rooms2 restaurants: Rafael's Steakhouse, Gazebo RestaurantCongress Lounge & BarGift shopBarber shop24-hour gymValet dry cleaning/shoeshineSmoking rooms available on request NeighborhoodAcross the street from Grant Park and the famous Buckingham Fountain, Congress Plaza rests on the main thoroughfare and shopping mecca of Michigan Avenue, aka, the Magnificent Mile. The hotel is walking distance from world-renowned institutions like the Art Institute of Chicago, Shedd Aquarium, and the fascinating Field Museum. Found on the banks of Lake Michigan, the Field Museum is the home of "Sue," the largest and most complete Tyrannosaurus Rex skeleton ever discovered, as well as a life-size Maori meeting house. Hints and tipsThe Congress is frequently nicknamed 'the most haunted hotel in Chicago,' and budding paranormal detectives should request a room in the oldest part of the building, the South Tower, for the 'highest chance' of ghostly activity.Be on the lookout for characters like notorious murder victim Peg Leg Johnny, or test your courage near the 12th floor room which was allegedly closed down due to paranormal activity.
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Nightly rates from $89

Club Quarters Central Loop

3 stars
4.1 / 5 541 reviews
Business traveler headquarters in Chicago's LoopThe Club Quarters Central Loop hotel might be mistaken for an office building with its subdued presence. A black awning marks this discrete spot and lends a sense of privacy. The hotel targets business travelers whose work brings them to the financial district and plays host to leisure travelers who want easy access to downtown attractions. Guests find great value for the location, price and attentive service, including a 24-hour concierge. The Club Quarters Central Loop hotel is within walking distance of several of Chicago's major attractions. Highlights Minutes from Michigan Avenue 24-hour concierge service Free high-speed wireless Internet throughout the hotel Elephant & Castle Pub and Restaurant next door RoomsThe clean and comfortable rooms at the Club Quarters Central Loop hotel keep the professional’s needs in mind. Ergonomic chairs and task lighting ease late work nights, while pillow-top mattress dressed in premium linens promise a refreshing night of sleep. Bookshelves display dictionaries and almanacs for a welcome scholarly touch. All rooms have complimentary wireless Internet access. FeaturesThe amenities at the Club Quarters Central Loop hotel are designed to keep guests productive. Find free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and five meeting rooms. Travelers looking to relax visit the restaurant and bar next door, exercise in the fitness room or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games.Free, chilled bottled water is available on each floor. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (8.9 mi/14.3 km) Blue Line (Jackson/Dearborn) (0.1 mi/0.2 km) Orange Line (Quincy/Wells) (0.1 mi/0.2 km) McCormick Place Convention Center (2.1 mi/3.3 km) Attractions Board of Trade (0.1 mi/0.2 km) Theater district (0.2 mi/0.3 km) Willis (formerly Sears) Tower (0.2 mi/0.4 km) Symphony Center (0.3 mi/0.5 km) Chicago Mercantile Exchange (0.3 mi/0.5 km) The Art Institute of Chicago (0.4 mi/0.6 km)
Value Rate includes up to 10% off
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Nightly rates from $80

Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 596 reviews
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like a celebrity and continues to make each stay at the Warwick Allerton Hotel Chicago as comfortable and rewarding as their predecessors did more than 80 years ago. Of all Magnificent Mile Chicago hotels, Warwick Allerton Hotel Chicago's historic Italian Renaissance style will dazzle you. The 443 guest rooms, including 84 suites, are perfect for your next Chicago meeting, banquet or wedding. The Warwick Allerton Hotel Chicago offers a variety of impressive, natural lit meeting rooms able to accommodate your group of 10 to 200. The Renaissance Ballroom located on the 23rd floor offers a stunning view of Michigan Avenue and Downtown Chicago. If you are looking for a luxury hotel in downtown Chicago, stay with us and experience our exquisite service and our great location. Welcome to the Warwick Allerton Hotel Chicago! Overnight valet parking $60 effective July 1st, 2013 A valid credit card must be presented at check-in for incidental charges.
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Nightly rates from $97

Red Roof Inn Chi Downtown Magnificent Mile

2 stars
2.8 / 5 152 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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Nightly rates from $73

The Silversmith Hotel Chicago

3 stars
4.2 / 5 227 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 $118
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Thu, Dec 11 - Tue, Dec 16 $167
Los Angeles Chicago Mon, Dec 15 - Fri, Jan 9 $257
Washington DC Chicago Thu, Nov 13 - Tue, Nov 18 $105
San Francisco Chicago Wed, Dec 3 - Thu, Dec 11 $255
Newark Chicago Thu, Nov 27 - Sun, Dec 7 $250
Atlanta Chicago Thu, Nov 13 - Tue, Nov 18 $105
Seattle Chicago Sat, Nov 15 - Wed, Nov 19 $289
Boston Chicago Wed, Nov 12 - Sat, Nov 15 $203
Dallas Chicago Wed, Dec 3 - Sat, Dec 6 $117
Denver Chicago Wed, Nov 12 - Sat, Nov 15 $137
Phoenix Chicago Thu, Nov 6 - Thu, Nov 13 $147
Orlando Chicago Tue, Dec 23 - Sat, Jan 3 $165
San Juan Chicago Wed, Nov 12 - Thu, Nov 20 $313
Mexico City Chicago Tue, Oct 28 - Wed, Oct 29 $369
Philadelphia Chicago Tue, Nov 25 - Sat, Nov 29 $249
San Diego Chicago Wed, Dec 3 - Tue, Dec 9 $285
Fort Lauderdale Chicago Tue, Nov 11 - Sat, Nov 15 $217
Las Vegas Chicago Wed, Nov 12 - Wed, Nov 19 $217
Guadalajara Chicago Thu, Oct 30 - Tue, Nov 4 $382
Tampa Chicago Fri, Nov 7 - Tue, Nov 11 $177
Houston Chicago Fri, Oct 31 - Wed, Nov 5 $115
Baltimore Chicago Fri, Oct 31 - Tue, Nov 11 $117
Honolulu Chicago Wed, Nov 19 - Mon, Nov 24 $698
Orange County Chicago Thu, Dec 4 - Wed, Dec 10 $314
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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.

Your trip

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