Cheap Chicago Vacations


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

Historic hotel on Michigan Avenue by Grant ParkGuests at the Congress Plaza Hotel at Grant Park hotel enjoy value prices and a convenient location across from Grant Park, Buckingham Fountain, Millennium Park, the Art Institute and Lake Michigan. Designed to accommodate large groups, the 850-room hotel has hosted legions of tourists, conventioneers and even the nation’s presidents since the World’s Columbian Exposition in 1893. Its presence among Chicago architecture is unmistakable: Just look for the oversized sign in all red caps. Highlights Spectacular views of Grant Park, Buckingham Fountain, Lake MichiganTwo restaurants and a lounge on site Wireless Internet in the lobby RoomsRooms at the Congress Plaza Hotel at Grant Park hotel favor space over flash. Find rooms and spacious suites of various sizes -- many with lakefront views -- as well as high ceilings and parlor seating. Complimentary wired and wireless Internet access are also available. FeaturesThe Congress Plaza Hotel at Grant Park serves as a top reception site for weddings, conferences and other formal events. The lobby with its massive mosaic-tiled ceiling inspires awe in both guests and architecture fans. More than 50,000 square feet of meeting space, including the gorgeous Gold Room with its gold-leaf covered walls and ceilings, lend opulence to any occasion.Diners visit the Gazebo Restaurant, a casual restaurant serving breakfast and lunch, or Rafael's Steakhouse, a more intimate dinner venue. Cocktails and pub fare are available in the lounge.Other property amenities include a barbershop, game room and fitness center. Transportation O’Hare International Airport (16.1 mi/25.8 km) Midway Airport (8.9 mi/14.4 km) Blue Line (LaSalle) (0.9 mi/1.5 km) Orange Line (Library) (0.3 mi/0.5 km) McCormick Place Convention Center (1.7 mi/2.7 km) Nearby attractions Grant Park (across the street) State Street (0.1 mi/0.2 km)Buckingham Fountain (0.3 mi/0.5 km)The Art Institute of Chicago (0.4 mi/0.6 km)Millennium Park (0.5 mi/0.9 km)Soldier Field (1 mi/1.6 km)The Magnificent Mile (1.3 mi/2.1 km) Policies and fees Valet Parking $44.00 for overnight parkingSelf-Parking $39.00 for overnight parking
Value Save 10% on your stay
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Hotel only
Nightly rates from $79

Raffaello Hotel

Boutique luxury in the heart of the Gold Coast In Chicago, the rule for downtown real estate is the closer to Lake Michigan, the more posh the address. Enter the Raffaello Hotel, a four-star hotel just steps from the lake and Magnificent Mile with a Michelin-rated chef and executive suites. Blending old-world aesthetics with modern conveniences, the hotel manages luxury and intimacy while being near the downtown hub. Stepping into the vintage building just off the tourist drag, guests are more likely to feel like Gold Coast residents than tourists. Raffaello Hotel offers Drumbar, a rooftop speakeasy-style inside lounge and outdoor garden terrace, found in the 18th floor. Highlights Walk to the Magnificent MileNext to the John Hancock CenterRooftop sundeckUpscale Italian fare at PelagoSanctuary fitness center with Precor fitness equipment RoomsStaying in this vintage building poses several advantages. The Raffaello Hotel offers rooms with high ceilings and architectural details for a unique, high-class vintage stay. Butterscotch-hued bedding and drapes match the walls, while high ceilings --painted stark white--stun with their beam construction. All rooms feature rainfall showerheads, GUYandGIRL amenities, 32-inch LCD TV, iHome and iPod players and 340-count linens. Rooms, which come in king, double double and suite versions are hard-wire and Wi-Fi enabled. Features Any Chicagoan will encourage a newcomer to put dining and an architectural experience on the itinerary. At the Raffaello Hotel, both needs are satisfied thanks to Pelago, the upscale Italian seafood restaurant and the rooftop garden, which is open from late spring to late fall. From the sundeck, guests can take in glorious views of the skyline, including Navy Pier and the next door neighbor: the John Hancock Center. Transportation O'Hare International Airport (18 miles)Midway Airport (12 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (11 minutes) Attractions John Hancock CenterAmerican Girl PlaceMagnificent MileOak Street ShoppingOak Street BeachNavy PierLake Michigan Policies and fees Wi-Fi access is complimentary. Standard Wi-Fi access fee with 3 MBPS that can connect up to three devices per day is $4.99 USD while Premium Wi-Fi access fee with 5 MBPS that can connect up to three devices per day is $9.99 USD.The hotel charges a $10 USD handling fee per storing package.The hotel charges a $25 USD for each additional guest.Photo identification and credit card are required at check in for incidental charges. If you do not provide a credit card, a cash security deposit in the amount of $1,000 is required.The hotel charges $61 USD for valet parking and $34 USD for self-parking.
Value Stay 3 nights, Save 35%
Flight + Hotel
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Hotel only
Nightly rates from $99

The Talbott Hotel

This Property is 100% Non-Smoking. The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is recognized as a leader in both leisure and business travel. It offers impeccable service with its concierge staff, all Les Clefs d'Or members, to assist with your evening plans or sightseeing. After a day of excitement, relax and unwind in your oversized guest room. The elegant marble bath stocked with fine Molton Brown Bath and Spa products in your guest room or your suite. Dry off with your luxurious Frette bath linens, and sink into a terrycloth robe while enjoying a program on your 42" LCD flat screen television with 30 High Definition Channels. Nightly turndown service; we will refresh your room, turn down your bed and leave you with delectable chocolate. You will be fully rested and ready to start another day of exploration after sleeping in one of our plush pillow top beds with luxurious linens, down pillows and comforter. Another day of relaxation and luxury awaits you tomorrow Imagine the rest. * Certified "Green Seal" Hotel. * 100% of the hotels electrical carbon footprint is offset by Wind Energy. * Four Diamond Rated by AAA. * Guests must be at least 21 years of age to check in. Valet Parking Rates 1 hour or less - staying at $22.00 1 - 3 hours - staying at $26.00 3 - 8 hours - increasing from $32.00 to $34.00 8 - 24 hours - increasing from $51.00 to $58.00 Little Market Brasserie - increasing from $13.00 to $14.00 Self Park - increasing from $36.00 to $40.00 with Validation otherwise $44.00 without. A $20 fee per person, per night will apply to all reservations where there are more than 2 people staying in a room and will be charged directly by the hotel. Extra beds are also available upon request for a fee of $24/night. See Front Desk for more information.
Value Stay tonight and save!
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Nightly rates from $145

The Whitehall Hotel

Gold Coast boutique meets 1920s charm The Whitehall Hotel manages that rare combination of location and ambiance. The hotel is situated one block from the Magnificent Mile and Rush Street nightlife district, but tucked away from the tourist fray on a residential street. One of Chicago's oldest luxury hotels but certainly no slouch, the Whitehall brims with 19th century elegance -- imagine chandeliers, wood paneling and tufted leather chairs, all restored to match the original European grace and grandeur of this Gold Coast gem. HighlightsOne block from the Magnificent Mile and Rush Street nightlifeWalk to John Hancock Center, Water Tower Place, Lake Michigan and Oak Street BeachDining at Fornetto Mei, a Pan-Italian restaurant Fitness center Rooms Chicago's independent boutique Whitehall Hotel, which has hosted guest celebrities like Katharine Hepburn, Richard Burton, Sophia Loren, Paul Newman, The Beatles and Mick Jagger over the years, provides intimate guest rooms and suites decorated with antique mahogany tables and nightstands, wood headboards, down duvets and marble bathrooms. High-speed Internet and wireless access are available in rooms (fees apply). FeaturesGuests at The Whitehall Hotel won't have to worry about leaving their dog or cat at home. The hotel welcomes pets less than 20 pounds for a non-refundable deposit. For an upscale casual dining option, dine at Fornetto Mei, which traverses Asia and Italy with its menu of oven-fired, thin crust pizza and house-made pot stickers or sample dumplings at Mei's Corner. A cozy atrium bar welcomes guests and invites sampling of the restaurant's 200 plus global and California boutique wines. Transportation O'Hare International Airport (15.3 mi/24.7 km)Chicago Midway Airport (9.7 mi/15.7 km)Blue Line (Washington/Dearborn) (1.1 mi/1.8 km)Orange Line (State/Lake) (0.9 mi/1.5 km)McCormick Place Convention Center (3.3 mi/5.3 km) AttractionsThe Magnificent Mile (0.1 mi/0.1 km)The Gold Coast (0.1 mi/0.2 km)Oak Street Beach (0.3 mi/0.4 km)Rush Street (1 block)Navy Pier (0.8 mi/1.3 km) Business Event space for six to 100 guestsBusiness center with computersHigh-speed Internet access (fees apply) Policies and feesGuests must be at least 21 years old to check in.Parking fee is $57 per night.The Whitehall Hotel is a 100% smoke free propertyInternet Access:Option 1: Includes Complimentary Internet Access 1.0 MBPS speed unlimited devices 24 hours per day.Option 2: Includes 2.5 MBPS speed of $9.95 per 24-hour period.Option 3: Includes 5.0 MBPS speed of $15.95 per 24-hour period.
Value Save 20% on non-refundable with advance purchase
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Nightly rates from $112

Chicago's Essex Inn

Affordable hotel south of Chicago's bustling downtown areaChicago's Essex Inn has an ideal location ideal on Michigan Avenue, just a few blocks south of the more congested areas of downtown Chicago. Grant Park is across the street, along with many famous Chicago attractions, including Millennium Park and the Art Institute. Sleek in design, the Essex Inn boasts a metal and glass lobby, floor-to-ceiling windows with city views and an impressive atrium housing a large pool. ADA-compliant areas are also available at Chicago's Essex Inn. Highlights Great value in the city for its location and amenitiesRooftop pool available year-roundLarge, well-equipped fitness room overlooks pool deck RoomsA color palette grounded in rich orange and brown earth tones keeps the scene warm. Floor-to-ceiling windows play up the hotel’s strongest asset, the city views. Flat-screen TVs and refrigerators are standard amenities in each room at Chicago's Essex Inn. Guests can have complimentary access to wireless Internet. Rooms also feature ADA-compliant areas. FeaturesIn a metropolis like Chicago, pools and green space are precious real estate. Chicago's Essex Inn has both. The garden pool feels like a competitive swimming complex, with a retractable atrium and global flags hanging from the rafters. The pool area features large windows that look out onto the well-manicured grounds of the rooftop garden. From the garden, guests enjoy skyline views of Grant Park and Lake Michigan from comfortable patio chairs and tables. Next to the pool is a large fitness center, featuring bikes, treadmills, weight machines, free weights, as well as six TVs.Visitors to Chicago who have come to sightsee take advantage of a hotel shuttle bus free of charge. It makes several stops along Michigan Avenue, including Water Tower Place. Other stops include Navy Pier and the Museum Campus.Travelers who want to stay connected access high-speed wireless Internet throughout hotel for a fee, or visit the 24-hour business center. Transportation O’Hare International Airport (16.1 mi/26 km) Chicago Midway Airport (8.7 mi/14.1 km) Blue Line (LaSalle to O’Hare) (3.8 mi/6.1 km) Orange Line (Roosevelt to Midway) (0.3 mi/0.5 km) McCormick Place Convention Center (1.5 mi/2.3 km) Nearby attractions Grant Park (0.5 mi/0.9 km)Millennium Park (0.8 mi/1.3 km)Lake Michigan (1.4 mi/2.2 km)The Magnificent Mile (1.5 mi/2.5 km)Museum Campus (3.1 mi/5 km) Business Six meeting rooms with space for 12 for 125 guests 24-hour business center with desktop computers, high-speed Internet access (fees apply) and a printer Complimentary high-speed wireless Internet available throughout Chicago's Essex Inn Policies and feesParking fee is $50 USD per night.
Value Save 15% on your stay
Flight + Hotel
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Hotel only
Nightly rates from $79
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Tue, Jun 10 - Thu, Jun 12 $208
Los Angeles Chicago Mon, May 5 - Tue, May 6 $274
Washington DC Chicago Sat, May 24 - Wed, May 28 $262
San Francisco Chicago Wed, May 28 - Sat, May 31 $318
Newark Chicago Sun, May 11 - Wed, May 14 $296
Atlanta Chicago Tue, Jun 3 - Wed, Jun 4 $242
Seattle Chicago Sun, May 11 - Thu, May 15 $322
Boston Chicago Tue, Jun 10 - Tue, Jun 17 $158
Dallas Chicago Tue, May 20 - Wed, May 28 $168
Denver Chicago Fri, May 30 - Tue, Jun 3 $158
Phoenix Chicago Sun, Apr 27 - Tue, Apr 29 $218
Orlando Chicago Tue, May 20 - Wed, May 21 $204
San Juan Chicago Thu, May 8 - Tue, May 13 $279
Mexico City Chicago Thu, May 15 - Tue, May 20 $466
Philadelphia Chicago Sat, Jun 14 - Wed, Jun 18 $284
San Diego Chicago Tue, Jun 10 - Tue, Jun 24 $288
Fort Lauderdale Chicago Tue, May 6 - Wed, May 7 $280
Las Vegas Chicago Wed, Jun 4 - Sun, Jun 8 $318
Guadalajara Chicago Tue, May 20 - Fri, May 23 $357
Tampa Chicago Mon, Jun 9 - Fri, Jun 13 $248
Houston Chicago Wed, May 28 - Sat, May 31 $207
Baltimore Chicago Wed, May 28 - Tue, Jun 3 $148
Honolulu Chicago Tue, May 6 - Tue, May 20 $890
Orange County Chicago Tue, May 20 - Thu, May 29 $278
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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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