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 1218 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 $116

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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Hotel only
Nightly rates from $134

River Hotel

3 stars
4.0 / 5 378 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
Flight + Hotel
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Hotel only
Nightly rates from $129

Hampton Inn & Suites Chicago-Downtown

3 stars
3.9 / 5 65 reviews
for big times in the big city... welcome to the Hampton Inn & Suites Chicago-Downtown hotel. The Hampton Inn & Suites® hotel in Downtown Chicago is right in the middle of the Windy City. We're just blocks away from many of Chicago's best attractions, from art museums to science centers, to shopping, and family fun. From our hotel in Chicago, you'll be able to blow through the Windy City, visiting famous sites like Millennium Park, Navy Pier and the Magnificent Mile. We're also central to scores of Chicago's top businesses. Our Downtown Chicago hotel offers great hotel specials and packages for the whole family on vacation or just a quick couple’s getaway.Regardless of whether you're in town for work or pleasure, our hotel in Downtown Chicago is your most convenient stop. Every morning, guests can enjoy our free Hampton On the House® hot breakfast or if you are in a hurry, grab one of our On the Run™ breakfast bags. There are also plenty of dining options around our Downtown Chicago hotel. We invite you to come stay with us at the Hampton Inn & Suites® hotel in Chicago-Downtown, where you're sure to enjoy big times in the big city. * Enjoy fine Italian dining at our onsite restaurant Rosebud Trattoria* Bring the family and enjoy a day at the Chicago Children’s Museum* Take advantage of our Blue Man Group package* Tour the city of Chicago on an exciting Segway adventure* Indulge in your own culinary adventure of Chicago by starting at La Madiaservices & amenitiesHere at the Hampton Inn Chicago, we're passionate about taking good care of you. That's why we offer a broad range of services and amenities to make your stay exceptional. Take a dip in our indoor pool or get a workout in our onsite fitness center. In town on business? Our convenient business center is open 24 hours a day and provides free internet access to help you get your work done.Whether you're planning a corporate meeting, special event or intimate wedding or need accommodations for a family reunion or your child's sporting group, we're delighted to offer you easy planning and booking tools to make the process quick and organized.* Take a video tour of our Downtown Chicago hotel* Meetings & Events in Downtown Chicago* Downtown Chicago area restaurant guide* Group rates for your wedding party, sporting team or famil
Value Free On The House hot breakfast, Wi-Fi
Flight + Hotel
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Nightly rates from $135

The Talbott Hotel

4 stars
4.6 / 5 1308 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!
Flight + Hotel
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Hotel only
Nightly rates from $168
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Tue, Jun 2 - Wed, Jun 10 $157
Los Angeles Chicago Tue, Jun 2 - Tue, Jun 9 $208
Washington DC Chicago Mon, Jun 8 - Fri, Jun 12 $145
San Francisco Chicago Wed, May 6 - Sat, May 30 $228
Newark Chicago Mon, May 18 - Tue, May 26 $232
Atlanta Chicago Wed, May 13 - Wed, May 27 $97
Seattle Chicago Tue, Jun 2 - Wed, Jun 3 $235
Boston Chicago Tue, Jun 2 - Wed, Jun 10 $147
Dallas Chicago Tue, May 19 - Wed, May 20 $81
Denver Chicago Tue, May 5 - Tue, May 12 $80
Phoenix Chicago Tue, May 5 - Mon, May 11 $204
Orlando Chicago Tue, Jun 2 - Wed, Jun 3 $175
San Juan Chicago Fri, Jun 5 - Sun, Jun 14 $346
Mexico City Chicago Thu, May 21 - Tue, Jun 16 $320
Philadelphia Chicago Tue, May 19 - Tue, May 26 $117
San Diego Chicago Wed, Jun 3 - Wed, Jun 10 $237
Fort Lauderdale Chicago Tue, Jun 2 - Wed, Jun 3 $117
Las Vegas Chicago Wed, May 6 - Tue, May 12 $159
Guadalajara Chicago Tue, May 12 - Tue, May 19 $340
Tampa Chicago Mon, May 11 - Wed, May 13 $127
Houston Chicago Wed, May 13 - Wed, May 27 $137
Baltimore Chicago Tue, Jun 2 - Tue, Jun 9 $177
Honolulu Chicago Wed, Apr 29 - Sun, May 3 $765
Orange County Chicago Sat, Jun 6 - Tue, Jun 9 $379
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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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