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 1292 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. LocationAcross 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. Highlights871 guestrooms36 suites23 meeting/event rooms2 restaurants: Rafael's Steakhouse, Gazebo RestaurantCongress Lounge & BarGift shopBarber shop24-hour gymValet dry cleaning/shoeshineSmoking rooms available on request
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Nightly rates from $116

Club Quarters Central Loop

3 stars
4.2 / 5 616 reviews
The 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. 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. Property 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. Highlights Minutes from Michigan Avenue 24-hour concierge service Free high-speed wireless Internet throughout the hotel Elephant & Castle Pub and Restaurant next door
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Nightly rates from $125

The Talbott Hotel

4 stars
4.6 / 5 1365 reviews
The Talbott Hotel is a European-style resort, which is reflected by the Italian Frette linen you'll find in each of its guest rooms. This AAA Four Diamond Hotel is a member of the Historic Hotels of America, as well as being one of the first Green Seal-certified hotels in the United States, so guests can be sure that their stay will have minimal impact on the environment. LocationWith 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. HighlightsWhen guests are not relaxing in their rooms, they can easily explore the downtown Chicago area thanks to the hotel's convenient location in the Gold Coast neighborhood. Go shopping at the Magnificent Mile, or for entertainment, Drury Lane Theater is located in Water Tower Place, while the Lookingglass Theater is located next to Water Tower Place. Rush Street is just outside the doors of the hotel and is famous for its nightclubs and restaurants. The Talbott Hotel will accept up to two well-behaved dogs per room with a combined weight of 50 pounds. Luxury pet boutique Tails in the City is located just across the street. The hotel houses one on-site restaurant, the Mercadito Fish Co, but the Signature Room on 95th, Tavern on Rush, and Merlot on Maple are a few of the dining options located close to the hotel. 
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Nightly rates from $165

River Hotel

3 stars
4.0 / 5 402 reviews
As 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. 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.   Property 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. 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
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Nightly rates from $152

Inn of Chicago, an Ascend Collection hotel

3 stars
3.5 / 5 286 reviews
In the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids and metallic embossed walls create drama and urban appeal. With its central location and focus on value, Inn of Chicago, an Ascend Collection hotel is a gem for business or leisure travelers seeking convenient access to the Magnificent Mile and its many diversions. RoomsThe rooms and suites at Inn of Chicago, an Ascend Collection hotel feel more like apartments than hotel rooms, and that's on purpose. Back in the 1920s, the former Hotel St. Clair offered one-bedroom apartments, and the effects linger today at the Inn of Chicago, an Ascend Collection hotel. Space for entertaining, working and lounging are separate from the sleeping area. Big picture windows with skyline views, photos of Chicago, zebra upholstery and unique layouts lend to a chic city vibe. In-room wireless Internet access is available for a fee. Property featuresGreat city views might well be the most valuable cache for Chicago hotels and for Inn of Chicago, an Ascend Collection hotel, this view comes at the Skyline Terrace on the 22nd floor. The Sky Suites also provide lofty views, while a dedicated party space accommodates up to 100 guests for weddings and other social events. Highlights Prime Chicago location just east of Magnificent Mile Free wireless Internet access in the lobby Complimentary stay for children under 18 The 22nd floor Skyline Terrace NOTE: Minimum check-in age is 18 years old.
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Nightly rates from $75
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Sat, Aug 22 - Sat, Aug 29 $167
Los Angeles Chicago Tue, Jul 14 - Fri, Jul 17 $228
Washington DC Chicago Tue, Aug 25 - Tue, Sep 1 $98
San Francisco Chicago Sun, Jul 19 - Thu, Aug 13 $217
Newark Chicago Wed, Jul 29 - Tue, Aug 4 $248
Atlanta Chicago Sat, Aug 22 - Sat, Aug 29 $99
Seattle Chicago Wed, Aug 26 - Wed, Sep 2 $330
Boston Chicago Thu, Aug 20 - Wed, Aug 26 $177
Dallas Chicago Sat, Aug 29 - Sat, Sep 12 $177
Denver Chicago Sun, Aug 23 - Wed, Aug 26 $153
Phoenix Chicago Thu, Aug 20 - Tue, Aug 25 $198
Orlando Chicago Tue, Aug 18 - Fri, Aug 21 $138
San Juan Chicago Fri, Aug 28 - Wed, Sep 9 $345
Mexico City Chicago Wed, Aug 26 - Sat, Aug 29 $351
Philadelphia Chicago Sat, Aug 22 - Wed, Aug 26 $100
San Diego Chicago Wed, Aug 19 - Wed, Sep 2 $267
Fort Lauderdale Chicago Tue, Jul 21 - Tue, Jul 28 $147
Las Vegas Chicago Tue, Aug 25 - Wed, Sep 2 $186
Guadalajara Chicago Wed, Aug 19 - Sun, Aug 30 $360
Tampa Chicago Wed, Jul 22 - Tue, Jul 28 $207
Houston Chicago Thu, Aug 20 - Fri, Aug 21 $157
Baltimore Chicago Wed, Jul 15 - Tue, Jul 21 $137
Honolulu Chicago Mon, Aug 3 - Tue, Aug 18 $888
Orange County Chicago Sun, Aug 23 - Thu, Aug 27 $253
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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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