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Hampshire

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Hampshire Flights as Low as $99

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Mon, Jul 14 - Tue, Jul 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 6 days ago
$99
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Jul 14 from Logan Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $99 found 6 days ago
Spirit Airlines
Mon, Jun 9 - Sat, Jun 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jun 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $102 found 5 days ago
JetBlue Airways
Mon, Jul 14 - Fri, Jul 18
BOS
Logan Intl.
ORD
O'Hare Intl.
$103 Roundtrip, found 6 days ago
$103
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Jul 14 from Logan Intl. to O'Hare Intl., returning Fri, Jul 18, priced at $103 found 6 days ago
Frontier Airlines
Mon, Jun 30 - Fri, Jul 4
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$105 Roundtrip, found 6 days ago
$105
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Jun 30 from Raleigh - Durham Intl. to O'Hare Intl., returning Fri, Jul 4, priced at $105 found 6 days ago
JetBlue Airways
Wed, May 28 - Sat, May 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $107 found 1 day ago
United
Wed, May 28 - Sat, May 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select United flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $107 found 1 day ago
United
Mon, Jun 30 - Wed, Jul 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 20 hours ago
$109
Roundtrip
found 20 hours ago
Select United flight, departing Mon, Jun 30 from Logan Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $109 found 20 hours ago
JetBlue Airways
Mon, Jun 30 - Wed, Jul 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 20 hours ago
$109
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Mon, Jun 30 from Logan Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $109 found 20 hours ago
American Airlines
Mon, Jun 30 - Wed, Jul 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 20 hours ago
$109
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Logan Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $109 found 20 hours ago
Delta
Wed, May 28 - Sat, May 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 28 from Logan Intl. to O'Hare Intl., returning Sat, May 31, priced at $117 found 1 day ago
United
Sat, Jun 7 - Sat, Jun 7
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 6 days ago
$135
Roundtrip
found 6 days ago
Select United flight, departing Sat, Jun 7 from Jacksonville Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $135 found 6 days ago
Frontier Airlines
Fri, Jul 4 - Mon, Jul 14
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 4 from Sacramento Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $191 just found
Delta
Wed, Jul 9 - Tue, Jul 15
DAL
Love Field
ORD
O'Hare Intl.
$200 Roundtrip, found 3 hours ago
$200
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Jul 9 from Love Field to O'Hare Intl., returning Tue, Jul 15, priced at $200 found 3 hours ago
Contour Airlines
Thu, Jul 10 - Sun, Jul 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Thu, Jul 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $209 found 5 days ago
Alaska Airlines
Tue, Aug 5 - Thu, Aug 14
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$354 Roundtrip, found 2 days ago
$354
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Aug 5 from Sacramento Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $354 found 2 days ago
Hawaiian Airlines
Mon, May 26 - Sat, May 31
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$458 Roundtrip, found 2 days ago
$458
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Mon, May 26 from Sacramento Intl. to O'Hare Intl., returning Sat, May 31, priced at $458 found 2 days ago

Cheap Flights to Hampshire

Fall in love at first flight with your vacation to Hampshire by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Hampshire on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Hampshire, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Hampshire

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Hampshire with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Hampshire?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Hampshire are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Hampshire?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Hampshire.

What airport is best to fly into Hampshire?

When you’re planning your trip to Hampshire, convenience is the name of the game. Luckily, Hampshire Dupage Airport is nearby so you can deplane and get going on checking off everything on your Hampshire must-do list.

How much are flights to Hampshire?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Hampshire on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $99, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Hampshire?

The trick to saving a stack of cash on your flight to Hampshire? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $99 right now, why wait?

Hampshire Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$99

Last Minute Hotel Deals in Hampshire

Super 8 by Wyndham Hampshire IL
Super 8 by Wyndham Hampshire IL
2 out of 5
115 Arrowhead Drive, Hampshire, IL
Book a stay at this business-friendly motel in Hampshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Goebbert's Farm and Donley's ...
6.6/10 (156 reviews)
"Good"

Reviewed on May 5, 2025

Get rates
Super 8 by Wyndham Hampshire IL
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,013 reviews)
"Room was big and comfortable"

Reviewed on May 14, 2025

Get rates
Hyatt Place Chicago/Hoffman Estates
Hilton Garden Inn Hoffman Estates
Hilton Garden Inn Hoffman Estates
3 out of 5
2425 Barrington Road, Hoffman Estates, IL
Stay at this 3-star hotel in Hoffman Estates. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,006 reviews)
"We had a wonderful stay at this Hilton with three minor exceptions: 1) The bathroom sink drains so slowly one had to stop running water every few minutes before proceeding to run more; 2). The room had 3 Kleenex tissues in the bathroom and then ran out. We had to go down to Registration desk to get ..."

Reviewed on May 12, 2025

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Hilton Garden Inn Hoffman Estates
MainStay Suites Chicago Hoffman Estates
MainStay Suites Chicago Hoffman Estates
2.5 out of 5
2875 Greenspoint Pkwy, Hoffman Estates, IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Woodfield Mall ...
7.8/10 Good! (1,007 reviews)
"Kitchen is nice, microwave, stove big fridge, laundry room, gym,"

Reviewed on May 11, 2025

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MainStay Suites Chicago Hoffman Estates
Country Inn & Suites by Radisson, Hoffman Estates, IL
Country Inn & Suites by Radisson, Hoffman Estates, IL
3 out of 5
2280 Barrington Rd, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,001 reviews)
"Great place to stay. Accommodations great. Patrick, was very accommodating, and welcoming"

Reviewed on May 7, 2025

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Country Inn & Suites by Radisson, Hoffman Estates, IL
Geneva Motel Inn
Geneva Motel Inn
2 out of 5
100 South Tyler Rd, St. Charles, IL
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7/10 Good! (831 reviews)
"Staff was great! We forgot a couple of items and when call was made they checked and called me. We appreciated it!"

Reviewed on May 4, 2025

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Geneva Motel Inn
Quality Inn and Suites St Charles - West Chicago
Quality Inn and Suites St Charles - West Chicago
2.5 out of 5
1600 E Main St, St. Charles, IL
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,005 reviews)
"Property was well kept and staff was pleasant and courteous."

Reviewed on May 11, 2025

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Quality Inn and Suites St Charles - West Chicago
Comfort Suites Elgin
Comfort Suites Elgin
2.5 out of 5
2480 Bushwood Drive, Elgin, IL
Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,003 reviews)
"I loved this hotel. So clean and new. I would definitely come back!"

Reviewed on May 12, 2025

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Comfort Suites Elgin
See all 260 properties in Hampshire
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.