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 1226 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.
Value Save 10% on your stay
Flight + Hotel
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Hotel only
Nightly rates from $134

Homewood Suites Chicago Downtown

3 stars
4.4 / 5 115 reviews
Home sweet Homewood A hot breakfast. Free Wi-Fi throughout the space. Gathering with others over wine, beer and soda. These daily conveniences might be missed while on vacation, but are customary amenities at Homewood Suites Chicago Downtown. Within walking distance of the Magnificent Mile and downtown Chicago restaurants, bars and shops, the River North Hilton property prides itself on the extras--regardless of whether the trip is for business or leisure. Highlights Complimentary daily hot breakfast buffetComplimentary Wi-Fi throughout the hotelFree nightly reception with meal, beer, wine and sodaFree grocery shopping serviceKing suites with full kitchens Rooms If these weren't hotel rooms, they might pass as city condos. Each space boasts two rooms and a full kitchen that includes a two-burner stove, microwave, dishwasher and refrigerator--ideal for a family looking to save money on dining expenses or an executive on an business trip. A wall separates the living, dining and sleeping quarters to provide maximum comfort. A palette of amber, brown and burgundy warms rooms, while several wall hangings add local flavor with images of Chicago landmarks. Guests sleep on the signature, plush Homewood Sweet Dreams mattress. LCD TV, two phone lines with voicemail and complimentary local calls are standard amenities. Features Homewood Suites Chicago Downtown provides a laundry list of bonuses that come at no extra cost to visitors. Expect a daily hot breakfast buffet, Wi-Fi throughout the space, a nightly reception with meal, beer, wine and soda, free coffee, tea or hot cider in the lobby all day, a grocery shopping service and a business center. During downtime, guests head to the indoor pool and cardio center, which are blessed with panoramic views of the Chicago skyline. Transportation O'Hare International Airport (16 miles)Midway Airport (11 miles)Closest train stops: Blue Line (Clark/Lake to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (11 minutes) Attractions Magnificent MileMuseum of Contemporary ArtNavy PierJohn Hancock CenterTribune TowerWrigley BuildingCivic Opera House Business More than 3,000 square feet of meeting spaceFree Wi-Fi throughout the hotelBusiness center with computer and printer
Value Free hot breakfast and high speed internet access
Flight + Hotel
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Nightly rates from $149

Club Quarters Wacker at Michigan

3 stars
4.0 / 5 576 reviews
Business hotel just off the Magnificent MileThe Club Quarters Wacker at Michigan Avenue hotel attends to the needs of the business traveler. Perched at a picturesque curve of Wacker Drive near the Chicago River, the hotel treats guests to professional amenities like complimentary Wi-Fi throughout the property, free use of a computer and printer, a 24-hour member service desk and concierge and ergonomic workstations in the rooms. Leisure travelers also find its close proximity to the Magnificent Mile and other Chicago attractions irresistible. Highlights 24-hour concierge and member services desk Free high-speed Internet access throughout the hotel Prime river and skyline viewsItalian restaurant on property RoomsThe Club Quarters Wacker at Michigan Avenue hotel maintains clean, basic rooms for single day, overnight and extended stays for mostly corporate clients. Some rooms have city or river views and all are equipped with ergonomic workstations, free Wi-Fi and reference books. In some studios and suites, visitors have the added conveniences of sofa beds and kitchenettes. FeaturesThe Club Quarters Wacker at Michigan Avenue hotel offers free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and meeting space for up to 1,000 guests. Guests ready for leisure time can exercise in the fitness room, or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games. Find free, chilled bottled water is offered on each floor. TransportationO’Hare International Airport (15.6 mi/25.1 km)Midway Airport (9.5 mi/15.3 km)Blue Line (State/Lake) (0.2 mi/0.3 km)Orange Line (State/Lake) (0.2 mi/0.3 km)McCormick Place Convention Center (2.6 mi/4.1 km) Attractions Marina City (0.1 mi/0.2 km)Chicago Cultural Center (0.3 mi/0.5 km)Millennium Park (0.4 mi/0.7 km)Michigan Avenue (0.4 mi/0.7 km)Chicago Mercantile Exchange (0.5 mi/0.8 km)Board of Trade (0.7 mi/1.2 km)Tribune Tower (0.8 mi/1.2 km)Grant Park (0.8 mi/1.3 km)The Magnificent Mile (1.1 mi/1.7 km)
Value Save 15% On Your Stay
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Nightly rates from $105

Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 642 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 $105

The Talbott Hotel

4 stars
4.6 / 5 1329 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 $155
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Wed, May 20 - Wed, May 27 $177
Los Angeles Chicago Sun, May 10 - Wed, May 13 $217
Washington DC Chicago Tue, Jun 2 - Wed, Jun 10 $145
San Francisco Chicago Mon, May 18 - Fri, May 29 $280
Newark Chicago Mon, May 25 - Sat, May 30 $253
Atlanta Chicago Sat, Jun 6 - Tue, Jun 9 $97
Seattle Chicago Wed, May 27 - Thu, Jun 4 $237
Boston Chicago Wed, May 27 - Wed, Jun 3 $147
Dallas Chicago Sat, Jun 6 - Wed, Jun 10 $81
Denver Chicago Sat, May 9 - Tue, May 12 $97
Phoenix Chicago Tue, Jun 2 - Wed, Jun 3 $238
Orlando Chicago Tue, May 26 - Tue, Jun 2 $175
San Juan Chicago Thu, Jun 4 - Tue, Jun 9 $358
Mexico City Chicago Sun, Jun 7 - Sun, Jul 5 $415
Philadelphia Chicago Tue, May 19 - Tue, May 26 $117
San Diego Chicago Tue, Jun 2 - Wed, Jun 17 $237
Fort Lauderdale Chicago Wed, May 20 - Sun, May 31 $117
Las Vegas Chicago Wed, May 13 - Tue, May 19 $137
Guadalajara Chicago Sun, May 17 - Fri, May 29 $418
Tampa Chicago Tue, Jun 9 - Tue, Jun 16 $145
Houston Chicago Mon, Jun 1 - Thu, Jun 4 $137
Baltimore Chicago Wed, May 13 - Mon, May 18 $177
Honolulu Chicago Mon, Jun 1 - Wed, Jun 3 $787
Orange County Chicago Tue, May 19 - Sat, May 23 $321
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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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